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Methylamine

Methylamine Structure
CAS No. 74-89-5
Chemical Name: Methylamine
Synonyms
Methanamine;CH3NH2;MeNH2;MONOMETHYLAMINE;AMINOMETHANE;methylamine solution;Methylamin;Aqueous METHYLAMINE;METHYLAMINE METHANOL;Methylamine water solution
CBNumber:
CB4387750
Molecular Formula:
CH5N
Molecular Weight:
31.06
MOL File:
74-89-5.mol
MSDS File:
SDS

Methylamine

Catalog No.
S560705
CAS No.
74-89-5
M.F
CH5N
CH3NH2
M. Wt
31.057 g/mol
Availability

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Methylamine

General Information

Researchers often face over-alkylation with ammonia or wrong N,N-dimethyl products with dimethylamine. Methylamine (CAS 74-89-5) eliminates these issues:

  • Superior nucleophilicity and minimal steric hindrance enable efficient SN2 amination for pharmaceuticals (ephedrine, theophylline).
  • Obligate C1 precursor ensures selective N-methylpyrrolidone (NMP) synthesis from gamma-butyrolactone.
  • In gold hydrometallurgy, it stabilizes thiosulfate as a synergistic ligand.

Supplied as anhydrous gas or 40% aqueous solution; ready for global dispatch.

CAS Number

74-89-5

Product Name

Methylamine

IUPAC Name

methanamine

Molecular Formula

CH5N
CH3NH2

Molecular Weight

31.057 g/mol

InChI

InChI=1S/CH5N/c1-2/h2H2,1H3

InChI Key

BAVYZALUXZFZLV-UHFFFAOYSA-N

SMILES

CN

solubility

greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
Very soluble in water
1 volume of water at 12.5 °C dissolves 1154 volumes of gas; at 25 °C dissolves 959 volumes of gas; 10.5 g is contained in 100 mL saturated benzene solution
Soluble in ethanol, benzene, and acetone; miscible with ether
Solubilities in various solvents at 1 atm and 20 °C.
Table: 255Q [Table#2189]
1080 mg/mL at 25 °C
Solubility in water at 25 °C: very good
Soluble

Synonyms

aminomethane, methylamine, methylamine bisulfite, methylamine hydride, methylamine hydrobromide, methylamine hydrochloride, methylamine hydrochloride, 14C-labeled, methylamine hydrofluoride, methylamine hydrogen cyanide, methylamine hydroiodide, methylamine ion (1-), methylamine nitrate, methylamine perchlorate, methylamine sulfate (1:1), methylamine sulfate (2:1), methylamine, 13C-labeled, methylamine, 14C-labeled, methylamine, 15N-labeled, methylamine, cesium salt, methylamine, monopotassium salt, methylamine, monosodium salt, methylammonium, methylammonium ion, monomethylamine, monomethylammonium ion

Canonical SMILES

CN

The exact mass of the compound Methylamine is unknown and the complexity rating of the compound is unknown. The solubility of this chemical has been described as greater than or equal to 100 mg/ml at 70° f (ntp, 1992)1080000 mg/l (at 25 °c)34.78 mvery soluble in water1 volume of water at 12.5 °c dissolves 1154 volumes of gas; at 25 °c dissolves 959 volumes of gas; 10.5 g is contained in 100 ml saturated benzene solutionsoluble in ethanol, benzene, and acetone; miscible with ether[‘solubilities in various solvents at 1 atm and 20 °c.’, ‘table: 255q [table#2191]’][]1080 mg/ml at 25 °csolubility in water at 25 °c: very goodsoluble. Its Medical Subject Headings (MeSH) category is Chemicals and Drugs Category – Organic Chemicals – Amines – Methylamines – Supplementary Records. It belongs to the ontological category of methylamines in the ChEBI Ontology tree. The United Nations designated GHS hazard class pictogram is Flammable;Compressed Gas;Corrosive;Irritant, and the GHS signal word is DangerThe storage condition is unknown. Please store according to label instructions upon receipt of goods.Use and application categories indicated by third-party sources: Fire Hazards -> Flammable – 4th degree. However, this does not mean our product can be used or applied in the same or a similar way.

Purity

40 wt% in H2O

Package Size

25 ml, 100 ml, 500 ml, 1 l

Methylamine Properties and Procurement

Methylamine (CAS: 74-89-5) is a fundamental primary aliphatic amine and the simplest organic derivative of ammonia. Commercially supplied as an anhydrous gas in pressurized cylinders or stabilized in aqueous (e.g., 40 wt%) and methanolic solutions, it serves as a critical C1 building block in industrial synthesis [1]. Its core procurement value proposition lies in its unhindered primary amine structure, which offers significantly higher nucleophilicity and basicity than ammonia, while avoiding the steric bulk and secondary-amine reactivity profile of dimethylamine. It is the obligate precursor for N-methylated derivatives across pharmaceutical, agrochemical, and specialized solvent manufacturing sectors.

Why Methylamine Cannot Be Substituted

Substituting methylamine with ammonia or higher alkylamines (such as dimethylamine or ethylamine) fundamentally alters reaction pathways and final product identities. For example, replacing methylamine with dimethylamine in the reaction with gamma-butyrolactone yields N,N-dimethyl derivatives instead of the target N-methylpyrrolidone (NMP), a critical battery and electronics solvent [1]. Similarly, using ammonia in SN2 alkylations results in sluggish kinetics and complex over-alkylation mixtures, whereas methylamine provides a precise balance of high nucleophilicity and a controlled steric profile to selectively yield secondary N-methyl intermediates without excessive byproduct formation.

Methylamine Evidence vs. Substitutes

Accelerated SN2 Kinetics

Methylamine exhibits vastly superior nucleophilicity compared to ammonia due to the +I inductive effect of the methyl group. In computational and experimental studies of SN2 ring-opening reactions, methylamine is calculated to react approximately 1.58 × 10^3 times faster than ammonia at specific hindered carbon centers [1].

Evidence Dimension Relative SN2 reaction rate
Target Compound Data ~1,580x relative rate (Methylamine)
Comparator Or Baseline 1.0x relative rate (Ammonia)
Quantified Difference >3 orders of magnitude faster reaction kinetics
Conditions SN2 amination of 2-methylthiirane at C3 (298.15 K)

Drastically reduces reaction times and improves yields for primary N-alkylation steps compared to using ammonia gas.

Enhanced Basicity and pH Control

The formal addition of a methyl group to ammonia significantly increases the thermodynamic basicity of the nitrogen lone pair. The conjugate acid of methylamine has a pKa of 10.64, compared to 9.25 for ammonium. This makes methylamine over 20 times more basic than ammonia in aqueous environments, though slightly less basic than dimethylamine (pKa 10.73) [1].

Evidence Dimension Conjugate acid pKa (in water)
Target Compound Data pKa = 10.64
Comparator Or Baseline pKa = 9.25 (Ammonia)
Quantified Difference +1.39 pKa units (~24.5x higher basicity)
Conditions Aqueous solution at 25 °C

Dictates the precise pH required for aqueous-organic biphasic extractions and ensures stable hydrochloride salt formation during pharmaceutical processing.

Obligate NMP Precursor

Methylamine is the strict, non-substitutable precursor for synthesizing N-methylpyrrolidone (NMP) via the continuous high-pressure, non-catalytic reaction with gamma-butyrolactone (GBL). Using dimethylamine or ammonia completely alters the product identity, making methylamine the sole viable C1 amine for this multi-million-ton industrial solvent workflow [1].

Evidence Dimension Target product identity
Target Compound Data Yields N-Methylpyrrolidone (NMP)
Comparator Or Baseline Dimethylamine (yields N,N-dimethyl amides)
Quantified Difference 100% divergence in product identity
Conditions Continuous liquid-phase reaction with gamma-butyrolactone at 150-220 °C

Procurement of exact monomethylamine is an absolute requirement for NMP manufacturing facilities; no homologues can be substituted.

Reduced Steric Hindrance

While secondary and tertiary amines possess higher intrinsic basicity, their steric bulk severely retards their nucleophilic attack on crowded electrophiles. Methylamine maintains an unhindered primary amine profile, allowing it to efficiently attack bulky substrates where trimethylamine reacts up to 270 times slower or fails entirely due to nonbonding repulsions [1].

Evidence Dimension Steric penalty in nucleophilic attack
Target Compound Data Unhindered primary amine attack (high reaction rate)
Comparator Or Baseline Trimethylamine (severe steric retardation)
Quantified Difference Avoids the >200-fold steric rate retardation seen in tertiary amines
Conditions Attack on sterically crowded electrophilic centers (e.g., 2,2-dimethylthiirane)

Ensures high conversion rates when synthesizing complex, sterically hindered active pharmaceutical ingredients (APIs).

Methylamine Application Scenarios

NMP Synthesis

Methylamine is directly utilized as the obligate C1 amine precursor in the continuous, high-pressure reaction with gamma-butyrolactone to produce NMP, a critical solvent for electronics and battery manufacturing [1].

N-Methylated API Manufacturing

Leveraging its high nucleophilicity and low steric hindrance, methylamine is the preferred reagent for the efficient SN2 amination of halogenated intermediates to produce pharmaceuticals such as ephedrine and theophylline [2].

Copper-Catalyzed Gold Leaching

In hydrometallurgy, methylamine acts as a synergistic ligand alongside ammonia in thiosulfate gold leaching. Its specific basicity and steric profile provide superior electrochemical stability to the copper complex, suppressing oxidative decomposition of thiosulfate [3].

Specification

Physical Description

Methylamine, anhydrous appears as a colorless gas or a liquid. Pungent fishy odor resembling odor of ammonia. The liquid boils at cold temperatures, hence it vaporizes rapidly when unconfined. Vapors are heavier than air and may collect in low-lying areas. Easily ignited under most conditions. Under prolonged exposure to intense heat the containers may rupture violently and rocket. Used for making pharmaceuticals, insecticides, paint removers, surfactants, rubber chemicals.
Methylamine, aqueous solution appears as a colorless to yellow aqueous solution of a gas. Odor ranges from fishlike to ammonia-like as the vapor concentration increases. Flash point (of 30% solution) 34 °F. Corrosive to skin and eyes. Less dense than water; vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
Liquid; Gas or Vapor, Liquid
Colorless gas with a fish- or ammonia-like odor; Note: A liquid below 21 degrees F. Shipped as a liquefied compressed gas; [NIOSH]
Liquid
COLOURLESS COMPRESSED LIQUEFIED GAS WITH CHARACTERISTIC ODOUR.
COLOURLESS SOLUTION IN WATER WITH PUNGENT ODOUR.
Colorless gas with a fish- or ammonia-like odor.
Colorless gas with a fish- or ammonia-like odor. [Note: A liquid below 21 °F. Shipped as a liquefied compressed gas.]

Color/Form

Colorless gas [Note: A liquid below 21 degrees F. Shipped as a liquefied compressed gas]
Flammable gas at ordinary temperature and pressure. Fuming liquid when cooled in ice and salt mixture.

XLogP3

-0.7

Hydrogen Bond Acceptor Count

1

Hydrogen Bond Donor Count

1

Exact Mass

31.042199164 g/mol

Monoisotopic Mass

31.042199164 g/mol

Boiling Point

20.3 °F at 760 mmHg (USCG, 1999)
20.66 °F at 760 mmHg (USCG, 1999)
-6.4 °C
BP: -6.3 °C at 760 mm Hg; -19.7 °C at 400 mm Hg; -32.4 °C at 200 mm Hg; -43.7 °C at 100 mm Hg; -73.8 °C at 10 mm Hg
-6 °C
48 °C
20.3 °F
21 °F

Flash Point

14 °F (Liquid) (NIOSH, 2024)
32 °F (USCG, 1999)
The Guide from the Emergency Response Guidebook is for “methylamine, anhydrous.” 32 °F
-10 °C (14 °F) – closed cup /Methylamine solution 30-50%/
32 °F (closed cup)
Flammable gas
-10 °C
NA (Gas) 14 °F (Liquid)

Heavy Atom Count

2

Vapor Density

1.1 (USCG, 1999) – Heavier than air; will sink (Relative to Air)
Saturated vapor density: 0.21270 lb/cu ft at 60 °F (Methylamine, anhydrous)
Relative vapor density (air = 1): 1.07
Relative vapor density (air = 1): 1.08
1.08

Density

0.693 at 20.3 °F (USCG, 1999) – Less dense than water; will float
0.6624 g/cu cm at 25 °C; 0.0014 g/cu cm at 101.33 kPa
Density: 0.656 g/cu cm at 25 °C (p>1 atm)
Saturated liquid density: 43.260 lb/cu ft; liquid heat capacity: 0.803 Btu/lb-F; liquid thermal conductivity: 1.516 Btu-inch/hr-sq ft-F; liquid viscosity: 0.250 Centipoise (all at 20 °F) (Methylamine anhydrous)
Relative density (water = 1): 0.7 (liquid)
Relative density (water = 1): 0.89
0.693 at 20.3 °F
0.70 (Liquid at 13 °F)
1.08(relative gas density)

LogP

-0.57
-0.57 (LogP)
log Kow = -0.57
-0.71
-0.6

Odor

Fish or ammonia-like odor

Odor Threshold

Odor Threshold Low: 0.0009 [ppm]
Odor Threshold High: 4.68 [ppm]
Detection odor threshold from AIHA (mean = 4.7 ppm)
The odor of methylamine is faint but readily detectable at less than 10 ppm, becomes strong at from 20 to 100 ppm and intolerably ammoniacal at 100 to 500 ppm.
Odor recognition in air= 2.10X10-2 ppm (purity not specified)
Low: 0.0252 mg/cu m; High: 12.0 mg/cu m

Decomposition

Hazardous decomposition products formed under fire conditions: Carbon oxides, nitrogen oxides (NOx) /Methylamine solution 30-50%/
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

Others

Melting Point

-134.5 °F (USCG, 1999)
-93.42 °C
-93.4 °C
-93 °C
-39 °C
-136 °F

UNII

BSF23SJ79E

Related CAS

14965-49-2 (hydriodide)
17000-00-9 (hydride)
22113-87-7 (nitrate)
33689-83-7 (sulfate[2:1])
593-51-1 (hydrochloride)
6876-37-5 (hydrobromide)

GHS Hazard Statements

Aggregated GHS information provided by 2202 companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;
H220 (67.03%): Extremely flammable gas [Danger Flammable gases];
H224 (32.88%): Extremely flammable liquid and vapor [Danger Flammable liquids];
H225 (17.76%): Highly Flammable liquid and vapor [Danger Flammable liquids];
H280 (16.76%): Contains gas under pressure;
may explode if heated [Warning Gases under pressure];
H302 (32.7%): Harmful if swallowed [Warning Acute toxicity, oral];
H314 (32.79%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];
H315 (84.88%): Causes skin irritation [Warning Skin corrosion/irritation];
H318 (91.14%): Causes serious eye damage [Danger Serious eye damage/eye irritation];
H319 (17.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];
H332 (96.41%): Harmful if inhaled [Warning Acute toxicity, inhalation];
H335 (93.69%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure;
Respiratory tract irritation];
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Use and Manufacturing

IDENTIFICATION: Methylamine is a colorless, flammable gas. It has a fish or ammonia-like odor. It mixes easily with water. USE: Methylamine is used as an intermediate in the synthesis of many products, including pharmaceuticals, insecticides, explosives, surfactants, and accelerators. It is commonly used in the tanning and dyeing industries. It is used as a fuel additive and as a photographic developer. It occurs naturally in a variety of vegetables and other foods, and has been found in cigarette smoke. Workers that produce or use methylamine may breathe in the gas or have direct skin contact. The general population may be exposed by breathing in contaminated air, or consumption of foods and contaminated drinking water. If methylamine is released to the environment, it will be broken down in air by reaction with hydroxyl radicals and ozone. It is not expected to be broken down in the air by sunlight. It will not volatilize into air from moist soil or water surfaces. It may volatilize into the air from dry soil surfaces. It is expected to move moderately through soil. It will be broken down by microorganisms. It is not expected to build up in fish. RISK: Temporary eye, nose, and throat irritation has been reported in humans following brief exposures to low-to-moderate levels of methylamine in the air. Data on the potential for methylamine to produce other toxic effects in humans were not available. Liquid methylamine liquid is a severe skin and eye irritant in laboratory animals, with severe damage following direct contact with undiluted liquid methylamine. Difficulty breathing, gasping for breath, congestion in the lungs and liver, damage to the eyes and skin, and death occurred in laboratory animals exposed briefly to extremely high air levels. Damage to the nasal tissues, mild liver changes, changes in the blood, and decreased body weights, were reported in laboratory animals following repeated exposure to high air levels of methylamine. Irritation to the gastrointestinal tract was observed following exposure to a high oral dose. Some animals died. Damage to the heart was reported in some laboratory animals following repeated exposure to moderate-to-high oral doses of methylamine. No evidence of infertility or abortion was observed in laboratory females exposed to low oral doses of methylamine prior to mating and throughout pregnancy, but the number of offspring born per mother was decreased. Data on the potential for methylamine to cause birth defects were not available. Data on the potential for methylamine to induce tumors in laboratory animals were not available. The potential for methylamine to cause cancer in humans has not been assessed by the U.S. EPA IRIS program, the International Agency for Research on Cancer, or the U.S. National Toxicology Program 14th Report on Carcinogens. (SRC)

Vapor Pressure

1972.92 mmHg at 60 °F (USCG, 1999)
2.65X10+3 mm Hg at 25 °C
Vapor pressure, kPa at 20 °C: 304
Vapor pressure, kPa at 20 °C: 31
3.0 atm

Pictograms

Flammable Irritant

Flammable;Compressed Gas;Corrosive;Irritant

Impurities

Typical commercial specifications.
Table: Specifications for Anhydrous Monomethylamine [Table#2184]
Table: Specifications for Aqueous Methylamine Solutions, Wt% [Table#2185]

Other CAS

74-89-5

Absorption Distribution and Excretion

Methylamine can be converted by semicarbazide-sensitive amine oxidase (SSAO) to formaldehyde and hydrogen peroxide, which have been proven to be toxic towards cultured endothelial cells. /The authors/ investigated whether or not these deaminated products from methylamine can exert potentially hazardous toxic effects in vivo. Long lasting residual radioactivity in different tissues was detected following administration of [14C]-methylamine in the mouse. Approximately 10% of the total administered radioactivity could even be detected 5 days after injection of [14C]-methylamine. Eighty percent of the formation of irreversible adducts can be blocked by a highly selective SSAO inhibitor, (E)-2-(4-fluorophenethyl)-3-fluoroallylamine hydrochloride (MDL-72974A). The residual radioactivity was primarily associated with the insoluble tissue components and the soluble macromolecules. Radioactively labelled macromolecules were fragmented following enzymatic proteolysis. Results suggest that the formaldehyde derived from methylamine interacts with proteins in vivo. In the streptozotocin-induced diabetic mice, both SSAO activity and the formation of residual radioactivity were found to be significantly increased in the kidney. Chronic administration of methylamine enhances blood prorenin level, which strongly suggests that uncontrolled deamination of methylamine may be a risk factor for initiation of endothelial injury, and subsequent genesis of atherosclerosis.
/MILK/ …The presence of volatile aliphatic amines … in human breast milk and amniotic fluid /was measured/ to assess their role in neonatal hypergastrinemia. These volatile nitrogenous amino acid metabolites have been previously demonstrated to stimulate gastrin release in in vivo and in vitro laboratory preparations. … The present study … demonstrated that these gastrin-stimulatory volatile amines were present in significant concentrations in breast milk during the first several weeks after parturition and in amniotic fluid. The individual amines that were identified in both human milk and amniotic fluid samples were methylamine, dimethylamine, ethylamine, trimethylamine, propylamine, isobutylamine, and butylamine. This study provides indirect evidence to support the possibility that the hypergastrinemia measured in the fetus/neonate during the period immediately before and after birth may be attributable, in part, to the ingestion of fluid containing high concentrations of gastrin-stimulating amines.
BACKGROUND: Dialysis adequacy is currently judged by measures of urea clearance. However, urea is relatively non-toxic and has properties distinct from large classes of other retained solutes. In particular, intracellularly sequestered solutes are likely to behave differently than urea. METHODS: We studied an example of this class, the aliphatic amine monomethylamine (MMA), in stable hemodialysis outpatients (n = 10) using an HPLC-based assay. RESULTS: Mean MMA levels pre-dialysis in end-stage renal disease subjects were 76 +/- 15 ug/L compared to 32 +/- 4 ug/L in normal subjects (n = 10) (P < 0.001). Mean urea reduction was 62% while the reduction ratio for MMA was 43% (P < 0.01). MMA levels rebounded in the 1 hour post-dialytic period to 85% of baseline, whereas urea levels rebounded only to 47% of baseline. MMA had a much larger calculated volume of distribution compared to urea, consistent with intracellular sequestration. Measures of intra-red blood cell (RBC) MMA concentrations confirmed greater levels in RBCs than in plasma with a ratio of 4.9:1. Because of the intracellular sequestration of MMA, we calculated its clearance using that amount removed from whole blood. Clearances for urea averaged 222 +/- 41 mL/min and for MMA 121 +/- 14 mL/min, while plasma clearance for creatinine was 162 +/- 20 mL/min (P < 0.01, for all differences). Using in vitro dialysis, in the absence of RBCs, solute clearance rates were similar: 333 +/- 6, 313 +/- 8 and 326 +/- 4 mL/min for urea, creatinine and MMA, respectively. These findings suggest that the lower MMA clearance relative to creatinine in vivo is a result of MMA movement into RBCs within the dialyzer blood path diminishing its removal by dialysis. CONCLUSION: In conclusion, we find that, in conventional hemodialysis, MMA is not cleared as efficiently as urea or creatinine and raise the possibility that RBCs may limit its dialysis not merely by failing to discharge it, but by further sequestering it as blood passes through the dialyzer.
In this study, we examined the effect of two creatine monohydrate supplementation regimes on 24-hr urinary creatine and methylamine excretion. Nine male participants completed two trials, separated by 6 weeks. Participants ingested 4 x 5 g x day(-1) creatine monohydrate for 5 days in one trial and 20 x 1 g x day(-1) for 5 days in the other. We collected 24-hr urine samples on 2 baseline days (days 1-2), during 5 days of supplementation (days 3-7), and for 2 days post-supplementation (days 8-9). Urine was assayed for creatine using high-performance liquid chromatography and methylamine using gas chromatography. Less creatine was excreted following the 20 x 1 g x day(-1) regime (49.25 +/- 10.53 g) than the 4 x 5 g x day(-1) regime (62.32 +/- 9.36 g) (mean +/- s; P < 0.05). Mean total excretion of methylamine (n = 6) over days 3-7 was 8.61 +/- 7.58 mg and 24.81 +/- 25.76 mg on the 20 x 1 g x day(-1) and 4 x 5 g x day(-1) regimes, respectively (P < 0.05). The lower excretion of creatine using 20 x 1 g x day(-1) doses suggests a greater retention in the body and most probably in the muscle. Lower and more frequent doses of creatine monohydrate appear to further attenuate formation of methylamine.
For more Absorption, Distribution and Excretion (Complete) data for Methylamine (8 total), please visit the HSDB record page.

Metabolism Metabolites

Methylamine Properties

Melting point -93 °C(lit.)
Boiling point -6.3 °C(lit.)
Density 0.785 g/mL at 25 °C
vapor density 1.08 (20 °C, vs air)
vapor pressure 27 psi ( 20 °C)
refractive index n20/D 1.371
Flash point 61 °F
storage temp. Store below +30°C.
solubility highly soluble in water (108g/100g) at 25°C; soluble in alcohol and miscible with ether; HCl salt is soluble in water and absolute alcohol; compound is insoluble in chloroform, acetone, ether, and ethyl acetate
pka 10.63(at 25℃)
form Gas
Specific Gravity 0.901 (20℃/4℃) (40% Soln.)
PH 14 (H2O, 20°C)
Odor Threshold 0.035ppm
explosive limit 4.9-20.8%
Water Solubility Miscible with water, ethanol, benzene, acetone and ether.
Specific Heat Capacity Cp(liquid): 3.29 J/(g·K); Cp(gas): 1.61 J/(g·K), at 25℃
Merck 14,6014
BRN 741851
Henry’s Law Constant (x 10-5 atmm3/mol): 1.11 at 25 °C (Christie and Crisp, 1967)
Exposure limits ACGIH:TLV-TWA 5 ppm (6.4 mg/m3); TLV-STEL 15 ppm (19 mg/m3)
OSHA:PEL-TWA 10 ppm (12 mg/m3)
NIOSH:REL-TWA 10 ppm
Dielectric constant 10.0(18℃)
Stability Stable. Highly flammable. Note wide explosion limits. Incompatible with oxidizing agents, acids, alkalies, alkaline earth metals, copper and its alloys, zinc and its alloys.
InChI 1S/CH5N/c1-2/h2H2,1H3
InChIKey BAVYZALUXZFZLV-UHFFFAOYSA-N
SMILES CN
LogP -0.570
CAS DataBase Reference 74-89-5(CAS DataBase Reference)
EPA Substance Registry System Methylamine (74-89-5)

 

SAFETY

Risk and Safety Statements

Symbol(GHS) Flame (GHS02)Corrosion (GHS05)Exclamation Mark (GHS07)
GHS02,GHS05,GHS07
Signal word Danger
Hazard statements H225-H314-H335
Precautionary statements P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
target organs Respiratory system
PPE Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes F+,Xn,C,F,T
Risk Statements 12-20-37/38-41-34-20/22-11-39/23/24/25-36/37/38-23/24/25-40-19
Safety Statements 7-16-26-36/37-45-29-36/37/39-3/7-3-39-33
OEB A
OEL TWA: 10 ppm (12 mg/m3)
RIDADR UN 1061 2.1 (METHYLAMINE, ANHYDROUS)
RIDADR UN 1235 3/PG II (METHYLAMINE, AQUEOUS SOLUTION)
WGK Germany 2
RTECS PF6300000
F 4.5-31
Autoignition Temperature 806 °F
TSCA TSCA listed
DOT Classification 2.1 (Flammable gas)
HazardClass 3
PackingGroup II
HS Code 29211100
Storage Class 3 – Flammable liquids
Hazard Classifications Acute Tox. 4 Oral
Carc. 2
Eye Dam. 1
Flam. Liq. 2
Skin Corr. 1B
STOT SE 3
Hazardous Substances Data 74-89-5(Hazardous Substances Data)
Toxicity LD50 orally in rats: 100-200 mg/kg (Kinney); LC50 in rats: 0.448 ml/l (Sarkar, Sastry)
IDLA 100 ppm
REACH Registrations Active
NFPA 704
4
3 0

Methylamine Chemical Properties,Uses,Production

Chemical Properties

Methylamine is a colorless, fi sh-like smelling gas at room temperature. It is used in a variety of industries, such as the manufacture of dyestuffs, treatment of cellulose, acetate rayon, as a fuel additive, rocket propellant, and in leather tanning processes.

Physical properties

Colorless, flammable gas with a strong ammonia-like odor. An experimentally determined recognition odor threshold concentration of 21 ppbv was reported by Leonardos et al. (1969). Odor threshold concentrations of 4.7 ppmv and 35 ppbv were experimentally determined by Nishida et al. (1979) and Nagata and Takeuchi (1990), respectively.

Uses

Methylamine is used in dyeing and tanning;in photographic developer, as a fuel additive,and as a rocket propellant. It is also usedin organic synthesis and as a polymerizationinhibitor. It occurs in certain plants, such asMentha aquatica.

Production Methods

Several methods are currently used for synthesis of methylamine. Virtually all produce a mixture of primary, secondary, and tertiary amines which can be continuously separated by distillation and extraction. The most commonly used synthesis involves heating ammonium chloride and methyl alcohol (ratio varies from 2:1 to 6:1, depending on desired ratio of amines) to about 300°C in the presence of a catalyst such as zinc chloride. Alternatively, methylamine can be synthesized by heating ammonium chloride and formaldehyde in the presence of H2 and a hydrogenation catalyst such as nickel or platinum. Methylamine is generally marketed as a liquid or a 33% aqueous solution (HSDB 1988).

Definition

ChEBI: The simplest of the methylamines, consisting of ammonia bearing a single methyl substituent.

General Description

A colorless gas or a liquid. Pungent fishy odor resembling odor of ammonia. The liquid boils at 20.3°F hence vaporizes rapidly when unconfined. Vapors are heavier than air and may collect in low-lying areas. Easily ignited under most conditions. Under prolonged exposure to intense heat the containers may rupture violently and rocket. Used for making pharmaceuticals, insecticides, paint removers, surfactants, rubber chemicals.

Air & Water Reactions

Highly flammable. Very soluble in water; the solutions are strongly basic and therefore corrosive. Liquid fumes in air.

Reactivity Profile

METHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Hazard

(Gas and liquid) Dangerous fire risk. Explosive limits in air 5–21%. Strong irritant to tissue. Eye, skin and upper respiratory tract irritant.

Health Hazard

Exposures to methylamine are known to cause adverse health effects among occupational workers. The workers demonstrate symptoms of toxicity that include, but are not limited to, irritation to the eyes, nose, and throat. Studies have indicated that the compound causes injury to the eyes through corneal opacities and edema hemorrhages in the conjunctiva, and injury to the liver. Studies of Guest and Varma indicated no signifi cant deleterious effects on the internal organs or skeletal deformities in experimental mice

Fire Hazard

FLAMMABLE. POISONOUS GASES MAY BE PRODUCED IN FIRE. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Toxic nitrogen oxides may be formed. Vapors are heavier than air and may travel considerable distance to a source of ignition and flash back.

Industrial uses

Methylamine and its hydrochloride salt are widely used in organic synthesis for introducing the methylamino group. In 1976, industrial consumption was 32,000 tons/year. One of its most important uses is in the preparation of amide-type surfactants. It is also used in the preparation of drugs such as adrenaline and synthetic caffeine. It serves as the base for more than twenty commercial products, among those included are photographic developers, insecticides, and antihistamine drugs (Beard and Noe 1981). It is also widely used in tanning and has been used in the separation of aromatics from aliphatic hydrocarbons (Sittig 1981).

Safety Profile

Poison by subcutaneous route. Moderately toxic by inhalation. A severe skin irritant. Mutation data reported. A strong base. Flammable gas at ordinary temperature and pressure. Very dangerous fire hazard when exposed to heat, flame, or sparks. Explosive when exposed to heat or flame. To fight fire, stop flow of gas. Forms an explosive mixture with nitromethane. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Potential Exposure

Methylamine is used in organic synthesis; a starting material for N-oleyltaurine, a surfactant; and p-N-methylaminophenol sulfate, a photographic developer. It has possible uses in solvent extraction systems in separation of aromatics from aliphatic hydrocarbons. It is also used in the synthesis of many different pharmaceuticals; pesticides and rubber chemicals.

Carcinogenicity

Methylamine was positive in the mouse lymphoma assay and negative in the Ames assay.

Environmental Fate

Photolytic. The rate constant for the reaction of methylamine and OH radicals in the atmosphere at 300 K is 1.3 x 10-13 cm3/moleculesec (Hendry and Kenley, 1979).
Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
Chemical/Physical. In an aqueous solution, chloramine reacted with methylamine to form Nchloromethylamine (Isaac and Morris, 1983).
Reacts with acids forming water-soluble salts.

storage

Methylamine is stored in a cool, well-ventilated noncombustible area separatedfrom possible sources of ignition andoxidizing substances and mercury. Itssolutions are stored in a flammable liquidstorage room or cabinet. The gas is shippedin steel cylinders or tank cars; the liquid isshipped in steel drums or tank cars.

Shipping

UN1061 Methylamine, anhydrous, Hazard Class: 2.1; Labels: 2.1-Flammable gas. UN1235 Methylamine, aqueous solution, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material. Cylinders must be transported in a secure upright position, in a well-ventilated truck. Protect cylinder and labels from physical damage. The owner of the compressed gas cylinder is the only entity allowed by federal law (49CFR) to transport and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express written permission of the owner.

Purification Methods

Dry the amine with sodium or BaO. It is commercially available in metal cylinders. [Beilstein 4 IV 118.]

Incompatibilities

A medium-strong base. Reacts violently with strong acids; mercury, strong oxidizers; nitromethane. Corrosive to copper, zinc alloys; aluminum, and galvanized surfaces.

Waste Disposal

Return refillable compressed gas cylinders to supplier. Controlled incineration (incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions).

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  1. CAS 74‑89‑5 corresponds to methylamine (CH₅N), a colorless, flammable gas with an ammonia‑like odor and a molecular weight of about 31.06.

    Overview

    Key Physical Properties

    Safety & Hazards

    Common Uses

    Methylamine is widely used in chemical synthesis, pharmaceuticals, agricultural chemicals, and as an intermediate in various industrial processes. This classification is consistent with its registry and safety documentation.

    Methylamine
    METHYLAMINE | Occupational Safety and Health Administration
    Methylamine safety precautions
    Methylamine chemical properties
    Methylamine industrial uses

    Methylamine | 74-89-5 – ChemicalBook

    Aug 25, 2026 · Incompatible with oxidizing agents, acids, alkalies, alkaline earth metals, copper and its alloys, zinc and its alloys. …

    • Boiling point: 6.3 °C (lit.)
    • Melting point: 93 °C (lit.)
    • Density: 0.785 g/mL at 25 °C
    • vapor density: 1.08 (20 °C, vs air)
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    Aug 25, 2026 · Methylamine (CAS 74-89-5) information, including chemical properties, structure, melting point, boiling point, density, …

    • Boiling point: 6.3 °C (lit.)
    • Melting point: 93 °C (lit.)
    • Density: 0.785 g/mL at 25 °C
    • vapor density: 1.08 (20 °C, vs air)
  2. Methylamine anhydrous, = 98 74-89-5 – MilliporeSigma

    Aldrich-295531; Methylamine anhydrous, >=98%; CAS No.: 74-89-5; Synonyms: Monomethylamine; Linear Formula: CH3NH2; …

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  8. Methylamine (CAS 74-89-5) | Pharma Intermediate | BenchChem

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    Methylamine

    NucleophilicityOrganic synthesisKinetics

    ⚠ Attention: For research use only. Not for human or veterinary use.
    Molecular FormulaCH5N
    CH3NH2
    CH5N
    CH3NH2
    Molecular Weight31.057 g/mol
    CAS No.74-89-5
    Cat. No.B109427
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    Technical Parameters


    Basic Identity
    Product Name Methylamine
    CAS 74-89-5
    Synonyms
    Molecular Formula CH5N
    CH3NH2
    CH5N
    CH3NH2
    Molecular Weight 31.057 g/mol
    Structural Identifiers
    SMILES CN
    InChI InChI=1S/CH5N/c1-2/h2H2,1H3
    InChIKey BAVYZALUXZFZLV-UHFFFAOYSA-N
    Commercial & Availability
    Standard Pack Sizes 100 ml / 250 ml / 1 l / Bulk Custom
    Availability In Stock
    Custom Synthesis Available on request
    Handling Information
    Solubility greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
    Very soluble in water
    1 volume of water at 12.5 °C dissolves 1154 volumes of gas;  at 25 °C dissolves 959 volumes of gas;  10.5 g is contained in 100 mL saturated benzene solution
    Soluble in ethanol, benzene, and acetone;  miscible with ether
    Solubilities in various solvents at 1 atm and 20 °C.
    Table: 255Q [Table#2189]
    1080 mg/mL at 25 °C
    Solubility in water at 25 °C: very good
    Soluble

    Structure & Identifiers


    Interactive Chemical Structure Model






    Methylamine Procurement Guide


    Methylamine (CAS 74-89-5), also known as monomethylamine (MMA) or methanamine, is the simplest primary aliphatic amine with the formula CH₃NH₂. This colorless gas (boiling point -6.3 °C) is a fundamental C1 building block and nucleophilic reagent extensively used in the synthesis of pharmaceuticals, agrochemicals, surfactants, and solvents [1]. It is commercially available in anhydrous form, as aqueous solutions (typically 30–40 wt%), and as solid hydrochloride salts to accommodate different process requirements [2]. Global methylamine consumption is driven by its role as a versatile chemical intermediate, with the chemical industry accounting for approximately 30% of total demand and projected steady growth across pharmaceutical and agrochemical sectors [3].

    Why Substitution Fails: Methylamine vs. Analogues


    Although methylamine belongs to the broader class of short-chain aliphatic amines—which includes ethylamine, dimethylamine, and ammonia—simple substitution among these compounds is rarely justifiable without process re-optimization due to quantifiable differences in nucleophilicity, basicity, steric profile, and product selectivity. As demonstrated by Mayr nucleophilicity parameters (N), the reactivity of methylamine (N = 13.85 in water) substantially exceeds that of ammonia (N = 9.48) and ethylamine (N = 12.87), while its pKa of 10.64 distinguishes it from both ammonia (pKa 9.26) and the more sterically hindered dimethylamine (pKa 10.73) [1][2]. Furthermore, in catalytic amination processes, methylamine exhibits fundamentally different shape-selective behavior compared to its higher alkyl homologs, with zeolite catalysts capable of achieving monomethylamine selectivities exceeding 70% under conditions where thermodynamic equilibria would otherwise favor trimethylamine [3]. These quantifiable differences in reaction kinetics, equilibrium distributions, and steric accessibility mean that substituting methylamine with an alternative amine necessitates revalidation of reaction yields, impurity profiles, and downstream purification steps—ultimately impacting both process economics and regulatory compliance.

    Quantitative Evidence: Methylamine vs. Comparators


    Nucleophilicity Advantage vs. Ammonia and Ethylamine

    Methylamine demonstrates significantly greater nucleophilic reactivity than its closest comparators ammonia and ethylamine as quantified by the Mayr nucleophilicity parameter N measured in water. Methylamine (N = 13.85, sN = 0.53) is 46% more nucleophilic than ammonia (N = 9.48, sN = 0.59) and approximately 8% more nucleophilic than ethylamine (N = 12.87, sN = 0.58) under identical aqueous conditions [1]. The replacement of one hydrogen in ammonia with a methyl group substantially increases nucleophilicity—an effect that exceeds what would be predicted based on basicity (pKaH) values alone [2]. This quantitative reactivity ranking (methylamine > ethylamine > ammonia) is consistent across multiple solvent systems including acetonitrile, where methylamine (N = 15.19) similarly outperforms ammonia (N = 11.39) [3].

    NucleophilicityOrganic synthesisKinetics

    Basicity and Steric Advantage for N-Methylation

    Methylamine exhibits a conjugate acid pKa of 10.64, which is 15% higher than ammonia (pKa = 9.26) and comparable to ethylamine (pKa = 10.81), while maintaining substantially lower steric bulk than dimethylamine (pKa = 10.73) or triethylamine (pKa = 10.75) [1][2]. This combination of enhanced basicity relative to ammonia paired with minimal steric hindrance is critical for selective N-methylation reactions. In pharmaceutical intermediate synthesis, methylamine consistently achieves higher selectivity for mono-N-methylated products compared to the sterically more demanding secondary amines, which can lead to undesirable over-alkylation and quaternary ammonium byproduct formation [3]. The pKa difference of ΔpKa = 1.38 between methylamine and ammonia corresponds to a 24-fold difference in proton affinity at equilibrium conditions.

    BasicitypKaN-methylation

    Zeolite Shape Selectivity for Monomethylamine

    In the catalytic synthesis of methylamines from methanol and ammonia, conventional amorphous silica-alumina catalysts produce a thermodynamic equilibrium mixture containing predominantly trimethylamine (TMA) with monomethylamine (MMA) selectivity limited to approximately 30 mol-% [1]. However, with shape-selective small-pore zeolite catalysts such as H-chabazite, MMA yields are substantially enhanced at higher ammonia partial pressures, while TMA formation is nearly completely suppressed due to transition-state selectivity within the zeolite micropores [2]. Sorption-desorption experiments demonstrate nearly complete exclusion of TMA from chabazite cages, enabling MMA selectivities >70% under optimized conditions [3]. This represents a >2.3-fold improvement in MMA selectivity compared to conventional non-shape-selective catalysts.

    Shape-selective catalysisZeoliteAmination

    Dielectric Constant and Organic Solubility vs. Ammonia

    Liquid methylamine (dielectric constant ε = 9.4 at 25 °C) exhibits significantly lower polarity than liquid ammonia (ε = 22.4), positioning it as a superior solvent for dissolving organic substances . This 58% lower dielectric constant translates to enhanced solubility for nonpolar and moderately polar organic compounds—a property analogous to the relationship between methanol (ε = 32.7) and water (ε = 78.5), where methanol serves as the preferred solvent for organic substrates [1]. The solvent properties of liquid methylamine are analogous to those of liquid ammonia but with demonstrably better organic solubility characteristics, making it particularly valuable for specialized organic transformations and extractions where ammonia would provide insufficient substrate solubility [2].

    Solvent propertiesDielectric constantOrganic solubility

    Gold Extraction Selectivity with Phosphorus Oxide Modifiers

    In the solvent extraction of gold from alkaline cyanide solutions, primary amines including methylamine demonstrate unique selectivity profiles when combined with Lewis base modifiers such as organic phosphorus oxides (e.g., tributyl phosphate, TBP) [1]. The apparent basicity of simple weak base amines with respect to Au(CN)₂⁻ can be increased by as much as 5 orders of magnitude through the addition of phosphorus oxide compounds, enabling selective gold extraction that is not achievable with alternative lixiviant systems [2]. While methylamine is one of several primary amines studied for this application, its minimal steric profile and favorable distribution coefficients distinguish it from bulkier amine extractants that may exhibit slower phase transfer kinetics or reduced selectivity for gold over base metal cyanide complexes [3].

    Solvent extractionGold recoveryHydrometallurgy

    Procurement Application Scenarios for Methylamine


    Selective N-Methylation in Pharmaceutical Intermediates

    Methylamine’s 46% higher nucleophilicity (N = 13.85) compared to ammonia (N = 9.48) and its minimal steric hindrance make it the preferred reagent for selective mono-N-methylation of pharmaceutical intermediates. This quantitative reactivity advantage enables clean conversion of ketone precursors to methylamino derivatives—as exemplified in ephedrine and pseudoephedrine synthesis where methylamine reacts with α-bromopropiophenone intermediates to form methylaminopropiophenone with high selectivity [1]. The combination of enhanced nucleophilicity and primary amine structure avoids the over-alkylation and quaternary ammonium byproduct formation frequently observed with secondary amines such as dimethylamine, reducing purification burden and improving overall process yield [2].

    Monomethylamine Production via Zeolite Catalysis

    For industrial methylamine production facilities, the implementation of shape-selective zeolite catalysts (specifically H-chabazite and modified ZK-5 zeolites) enables monomethylamine selectivities exceeding 70 mol-% compared to the ≤30 mol-% achievable with conventional amorphous catalysts [3]. This >2.3-fold improvement in MMA selectivity directly addresses the market-driven demand for mono- and dimethylamines over the thermodynamically favored trimethylamine, significantly reducing downstream separation costs and improving overall process economics [4]. Procurement decisions for methylamine supply should consider whether the manufacturer utilizes shape-selective catalyst technology, as this directly impacts product purity and cost competitiveness [5].

    Specialty Solvent for Enhanced Organic Solubility

    Liquid methylamine (ε = 9.4) serves as a superior solvent compared to liquid ammonia (ε = 22.4) for organic transformations involving nonpolar or moderately polar substrates that exhibit limited solubility in ammonia. The 58% lower dielectric constant translates to demonstrably higher organic solubility, expanding the scope of reactions that can be conducted in this solvent system . Applications include specialized organic syntheses, Birch-type reductions, and solvent extractions where the solubility advantages of methylamine over ammonia can reduce solvent volume requirements and improve reaction homogeneity [6].

    Gold Recovery with Amine-Modifier Systems

    In hydrometallurgical gold recovery, methylamine—when combined with organic phosphorus oxide modifiers such as TBP or DBBP—enables selective solvent extraction of gold from alkaline cyanide solutions with apparent basicity enhancements of up to 5 orders of magnitude [7]. This application leverages the primary amine’s favorable steric profile and distribution coefficients to achieve selective Au(CN)₂⁻ extraction over competing base metal cyanide complexes. This represents a quantitatively validated alternative extraction pathway that addresses the environmental and safety concerns associated with conventional cyanide processing while maintaining competitive recovery efficiencies

    1. Methylamine (CAS 74-89-5) | Pharma Intermediate | BenchChem

      Buy Methylamine (CAS 74-89-5) from BenchChem. High-nucleophilicity C1 building block with 46% greater reactivity than ammonia, …

      • CAS: 74-89-5
      • Molecular Weight: 31.057 g/mol
      • Molecular Formula: CH5NCH3NH2CH5NCH3NH2
      • Product Name: Methylamine
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    3. Methylamine | 74-89-5 – ChemicalBook

      Aug 25, 2026 · Methylamine (CAS 74-89-5) information, including chemical properties, structure, melting point, boiling point, density, …

      • Boiling point: 6.3 °C (lit.)
      • Melting point: 93 °C (lit.)
      • Density: 0.785 g/mL at 25 °C
      • vapor density: 1.08 (20 °C, vs air)
    4. Methylamine anhydrous, = 98 74-89-5 – MilliporeSigma

      Aldrich-295531; Methylamine anhydrous, >=98%; CAS No.: 74-89-5; Synonyms: Monomethylamine; Linear Formula: CH3NH2; …

    5. Methylamine | 74-89-5 – ChemicalBook

      Aug 25, 2026 · Methylamine and its hydrochloride salt are widely used in organic synthesis for introducing the methylamino group. In …

    6. Methylamine | 74-89-5 | TCI AMERICA

      Jul 26, 2026 · Product # M0137 CAS RN 74-89-5 Purity / Analysis Method: View Full Details Methylamine (ca. 7% in …

    7. Methylamine | CAS 74-89-5 | SoleChem

      Methylamine (CAS 74-89-5), also referenced industrially as MeNH2, is a primary aliphatic amine; a compressed gas or aqueous …

    8. Methylamine | 74-89-5 | TCI AMERICA

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