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Sodium borohydride (CAS 16940-66-2)

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Alternate Names:
Sodium tetrahydroborate
Application:
Sodium borohydride is a strong reducing agent used in organic and biochemical reactions
CAS Number:
16940-66-2
Purity:
≥98%
Molecular Weight:
37.83
Molecular Formula:
NaBH4
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Available in US only.
* Refer to Certificate of Analysis for lot specific data.

Sodium borohydride

Sodium borohydride Structure
CAS No.
16940-66-2
Chemical Name:
Sodium borohydride
Synonyms
NaBH4;SODIUM TETRAHYDROBORATE;SBH;SODIUM TETRAHYDRIDOBORATE;AF;BH4Na;sodiumborohydrate;Natriumtetrahydroborat;SODIUM BOROHYDRIDE CAPLETS;Sodium borohydride, 98% min
CBNumber:
CB5322426
Molecular Formula:
BH4Na
Molecular Weight:
37.83
MOL File:
16940-66-2.mol
MSDS File:
SDS
Modify Date:

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Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

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Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Buy Sodium borohydride Cas 16940-66-2

Sodium borohydride Properties

Melting point >300 °C (dec.) (lit.)
Boiling point 500°C
bulk density 350-500kg/m3
Density 1.035 g/mL at 25 °C
vapor pressure <1 hPa (25 °C)
Flash point 158 °F
storage temp. Store at RT.
solubility Methanol (Slightly), Water (Soluble)
form tablets
Specific Gravity 1.4
color White
PH 11 (10g/l, H2O, 20℃)
explosive limit 3.02%(V)
Water Solubility 550 g/L (25 ºC)
Specific Heat Capacity Cp(crystal): 2.29 J/(g·K), at 25℃
Sensitive Hygroscopic
Merck 14,8592
Stability Stability Stable, but reacts readily with water (reaction may be violent). Incompatible with water, oxidizing agents, carbon dioxide, hydrogen halides, acids, palladium, ruthenium and other metal salts, glass. Flammable solid. Air-sensitive.
Cosmetics Ingredients Functions BULKING
ANTIOXIDANT
SKIN CONDITIONING
InChI 1S/BH4.Na/h1H4;/q-1;+1
InChIKey YOQDYZUWIQVZSF-UHFFFAOYSA-N
SMILES [BH4-].[Na+]
CAS DataBase Reference 16940-66-2(CAS DataBase Reference)
NIST Chemistry Reference Sodium tetrahydroborate(16940-66-2)
EPA Substance Registry System Sodium borohydride (16940-66-2)

SAFETY

Risk and Safety Statements

Symbol(GHS) Flame (GHS02)Corrosion (GHS05)Skull and Crossbones (GHS06)Health Hazard (GHS08)
GHS02,GHS05,GHS06,GHS08
Signal word Danger
Hazard statements H260-H301-H314-H360F
Precautionary statements P201-P231+P232-P280-P308+P313-P370+P378-P402+P404
PPE Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes F,T,N,C,Xn
Risk Statements 60-61-15-34-23/24/25-24/25-35-21/22-51/53-42/43-49-63-62-36/38-43-19-68-50/53
Safety Statements 53-43-45-43A-36/37/39-26-22-50-36/37-61
RIDADR UN 1426
WGK Germany 2
RTECS ED3325000
F 10-21
Autoignition Temperature 220 °C
TSCA TSCA listed
HazardClass 4.3
PackingGroup I
HS Code 28500090
Storage Class 4.3 – Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications Acute Tox. 3 Oral
Eye Dam. 1
Repr. 1B
Skin Corr. 1B
Water-react 1
Hazardous Substances Data 16940-66-2(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 160 mg/kg LD50 dermal Rabbit 230 mg/kg
REACH Registrations Active
Limited Quantities 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities Not Permitted as Excepted Quantity
NFPA 704
1
2 2
W

Sodium borohydride Chemical Properties,Uses,Production

Chemical Properties

Sodium Borohydride is a white, odorless powder or pellet. It is used for bleaching wood pulp, as a blowing agent for plastics, and as a reducing agent for aldehydes and ketones.

Physical properties

White cubic crystals; hygroscopic; density 1.07 g/cm3; decomposes slowly at about 400°C in vacuum or in moist air; soluble in water, decomposing and evolving hydrogen; also soluble in alcohols, liquid ammonia, amines and pyridine.

Preparation

Sodium borohydride is prepared by reacting sodium hydride with trimethyl borate at about 250°C: 4 NaH + B(OCH3)3 → NaBH3 + 3NaOCH3
Also, sodium borohydride can be made by passing diborane, B2H6, through a solution of sodium methylate, NaOCH3 , in methanol: 2B2H6 + 3NaOCH3→ 3NaBH3 + B(OCH3)3
Alternatively, diborane may be be passed through a solution of sodium tetramethoxyborohydride at low temperatures: 3 NaB(OCH3)3 + 2B2H6 → 3NaBH3 + 4B(OCH3)3.

Production Methods

Sodium bisulfate is a by-product of sodium sulfate manufacture. One process involves reacting sulfuric acid with sodium nitrate at high temperature to form nitric acid and sodium bisulfate: NaNO3 + H2SO3 → NaHSO4 + HNO3(g)
In the above reaction, nitric acid is obtained as vapor. It is purged from the system and collected in water to obtain nitric acid solution of desired concentration. Sodium bisulfate is separated by fractional crystallization.

Definition

ChEBI: Sodium borohydride is an inorganic sodium salt and a metal tetrahydridoborate.

General Description

Sodium borohydride is a white to grayish crystalline powder. Sodium borohydride is decomposed by water to form sodium hydroxide, a corrosive material, and hydrogen, a flammable gas. The heat of this reaction may be sufficient to ignite the hydrogen. The material itself is easily ignited and burns vigorously once ignited. Sodium borohydride is used to make other chemicals, treat waste water, and for many other uses.

Air & Water Reactions

Hydrolysis generates enough heat to ignite adjacent combustible material [Haz. Chem. Data 1966]. Dissolves in water with liberation of heat, may steam and spatter. Solution is basic (alkaline). Reaction of water with the borohydride liberates flammable hydrogen gas. Sodium borohydride burns in air [Lab. Gov. Chemist 1965].

Reactivity Profile

Sodium borohydride is a powerful reducing agent. A chemical base. Absorbs moisture readily forming caustic solution. which attacks aluminum and zinc. A violent polymerization of acetaldehyde results from the reactions of acetaldehyde with alkaline materials such as sodium hydroxide. Calcium oxide or sodium hydroxide react with phosphorus pentaoxide extremely violently when initiated by local heating [Mellor 8 Supp.3:406 (1971]. Using potassium hydroxide to dry impure tetrahydrofuran, which contains peroxides, may be hazardous. Explosions have occurred in the past. Sodium hydroxide behaves in a similar way as potassium hydroxide [NSC Newsletter, Chem. Soc. 1967]. Ignition occurs if a mixture of the hydride and sulfuric acid is not cooled. Contact of glycerol and Sodium borohydride leads to ignition, other glycols and methanol are exothermic but do not ignite.

Hazard

Reacts with water to evolve hydrogen and sodium hydroxide. Flammable, dangerous fire risk. Store out of contact with moisture.

Health Hazard

It is mildly corrosive to skin. Oral intake orintravenous administration of the solid or itssolution produced high toxicity in animals.Ingestion of 160-mg/kg dose was lethal torats (NIOSH 1986).

Fire Hazard

Behavior in Fire: Decomposes and produces highly flammable hydrogen gas.

Safety Profile

Poison by ingestion and intraperitoneal routes. A strong alkali. A severe eye, skin, and mucous membrane irritant. Ignites in air above 288’C when exposed to spark. Potentially explosive reaction with aluminum chloride + bis(2-methoxyethyl) ether. Reacts with ruthenium salts to form a solid product which explodes when touched or on contact with water. Reacts to form dangerously explosive hydrogen gas on contact with alkali, water and other protic solvents (e.g., methanol, ethanol, ethylene glycol, phenol), aluminum chloride + bis(2methoxyethy1)ether. Reacts violently with anhydrous acids (e.g., sulfuric, phosphoric, fluorophosphoric) to form diborane. Violent exothermic reaction with dimethyl formamide has caused industrial explosions. Mixtures with sulfuric acid may ignite. Incompatible with palladium, diborane + bis(2-methoxyethyl) ether, polyglycols, dimethylacetamide, oxidizers, metal salts, finely divided metallic precipitates of cobalt, nickel, copper, iron, and possibly other metals. Emits flammable vapors on contact with acid fumes. Materials sensitive to polymerization under alkaline conditions, such as acrylonitrile, may polymerize upon contact with sodium borohydride. Avoid storage in glass containers. When heated to decomposition it emits toxic fumes of NanO. See also HYDRIDES, BORON COMPOUNDS, and SODIUM COMPOUNDS.

Purification Methods

After adding NaBH4 (10g) to freshly distilled diglyme (120mL) in a dry three-necked flask fitted with a stirrer, nitrogen inlet and outlet, the mixture is stirred for 30minutes at 50o until almost all of the solid has dissolved. Stirring is stopped, and, after the solid has settled, the supernatant liquid is forced under N2 pressure through a sintered-glass filter into a dry flask. [The residue is centrifuged to obtain more of the solution which is added to the bulk.] The solution is cooled slowly to 0o and then decanted from the white needles that separated. The crystals are dried by evacuating for 4hours to give anhydrous NaBH4. Alternatively, after the filtration at 50o the solution is heated at 80o for 2hours to give a white precipitate of substantially anhydrous NaBH4 which is collected on a sintered-glass filter under N2, then evacuated at 60o for 2hours [Brown et al. J Am Chem Soc 77 6209 1955]. NaBH4 has also been crystallised from isopropylamine by dissolving it in the solvent at reflux, cooling, filtering and allowing the solution to stand in a filter flask connected to a Dry-ice/acetone trap. After most of the solvent has passed over into the cold trap, crystals are removed with forceps, washed with dry diethyl ether and dried under vacuum. [Kim & Itoh J Phys Chem 91 126 1987.] Somewhat less pure crystals were obtained more rapidly by using Soxhlet extraction with only a small amount of solvent and extracting for about 8hours. The crystals that formed in the flask are filtered off, then washed and dried as before. [Stockmayer et al. J Am Chem Soc 77 1980 1955.] Other solvents used for crystallisation include water and liquid ammonia.

Waste Disposal

It may be destroyed in several ways. Onemethod is as follows (Aldrich 1995). Thesolid or its solution is dissolved or diluted inlarge volume of water. Diluted acetic acid oracetone is then slowly added to this solutionin a well-ventilated area. Hydrogen generatedfrom decomposition of borohydride shouldbe carefully vented out. The pH is adjustedto 1. The solution is then allowed to stand forseveral hours. It is then neutralized to 7, andthe solution is then evaporated to dryness.The residue is then buried in a landfillsite approved for hazardous waste disposal.Sodium borohydride may be destroyed in thelaboratory by alternative methods mentionedfor other hydrides.

Sodium borohydride Preparation Products And Raw materials

Raw materials

Sodium hydride Sodium Boric acid Hydrogen Methanol
Sulfuric acid Isoquinoline-1-carboxylic acid

Preparation Products

Borane-pyridine complex tert-Butyl 4-(hydroxymethyl)pyridin-2-ylcarbamate 3-Bromo-cyclopent-2-enol 9-Anthracenemethanol DL-Phenylalaninol
3-Bromobenzyl alcohol Rocuronium bromide 4-Bromobenzyl alcohol Desogestrel beta-Methylphenethyl alcohol
N,N-Dimethyl-4-[(methylamino)methyl]aniline (2,6-Dichloro-3-nitro)benzyl alcohol 3,5-Dimethoxybenzyl bromide 3,5-Dimethoxybenzyl alcohol Methyl-(2-trifluoromethyl-benzyl)-amine
4-Trifluoromethylbenzyl chloride Atorvastatin Ethyl 6-(hydroxymethyl)pyridine-2-carboxylate Cycloleucinol Tetrabutylammonium borohydride
(1H-Imidazol-2-yl)-methanol CARUMONAM Dulcitol acid washing corrosion inhibitor Sx-1 (3-Fluorobenzyl)methylamine
4,4-Dimethylcyclohexan-1-ol (1H-Imidazol-2-ylmethyl)-methyl-amine 3-Methoxy-N-methylbenzylamine 97 2-Hydroxy-3-methoxybenzyl alcohol 5-Methyl-2-hexanol
Ethyl 6-(chloromethyl)pyridine-2-carboxylate (S)-(-)-2-Methyl-1-butanol 2-Methoxy-N-methylbenzylamine hydrochloride ,97% 6-(Aminomethyl)pyridine-2-carbohydrazide N-(4-Methoxybenzyl)-N-methylamine
1-Methylcyclohexanol 3-Chloro-N-methylbenzylamine 2-Hydroxy-6-chloroquinoxaline 2-chloro-5-ethylaminomethylpyridine 9-(Chloromethyl)anthracene

Sodium borohydride Spectrum

Sodium borohydride(16940-66-2)IR1Sodium borohydride(16940-66-2)Raman

16940-66-2(Sodium borohydride)Related Search:

Sodium chloride Sodium hydroxide Sodium sulfate Sodium acetate Diclofenac sodium
Sodium benzoate Trisodium phosphate Sodium chlorite Sodium bicarbonate Potassium borohydride
Lithium borohydride Sodium cyanoborohydride Sodium tetraphenylboron SODIUM BORODEUTERIDE SODIUM CYANOBORODEUTERIDE
Sodium triacetoxyborohydride Sodium tetraethylborate Sodium tri-sec-butylborohydride
VenPure? SF SodiuM borohydride caplets (18 x 10 x 8 MM), 98% SodiuM borohydride granular, 10-40 Mesh, 98% SodiuM borohydride granular, 99.99% trace Metals basis SodiuM borohydride powder, >=98.0% SodiuM borohydride puruM p.a., >=96% (gas-voluMetric) SodiuM borohydride ReagentPlus(R), 99% SodiuM borohydride solution 2.0 M in triethylene glycol diMethyl ether SodiuM borohydride(pellet,powder) 26S proteasome non-ATPase regulatory subunit 4 Antisecretory factor-1 Sodium borohydride 90% NaBH4 basis, pellets, diam. 8 mm, Cobalt (Doped) Sodium borohydride on aluminum oxide extent of labeling: ~10 wt. % loading, matrix basic alumina support Sodium borohydride purum, >=97.0% (gas-volumetric), tablets Sodium borohydride solution 0.5 M in 2-methoxyethyl ether Sodium borohydride solution SWS, ~12 wt. % in 14 M NaOH VenPure VenPure? AF Sodium Borohydride 〔Sodium Tetrahydroborate〕 Sodium borohydride (fine granular) Msynthplus Sodium borohydride, 7/16 in., 98% Sodium borohydride, 20% aq. NaOH solution Sodium borohydride, Stable aq. soln. hidkitexdf Sodium tetrahydroborate(1-) sodiumborohydrate sodiumborohydride(na(bh4)) sodiumborohydride,powder sodiumhydroborate sodiumtetrahydridoborate(1-) sodiumtetrahydroborate(1-) tetrahydro-borate(1-sodium COBALT-DOPED SODIUM BOROHYDRIDE Sodiuu borohydride Sodium borohydride, 98% min Sodium borohydride, 97+% Sodium Borohydride, 99%, Granular SODIUM BOROHYDRIDE extrapure Sodium tetrahydridoborate, VenPure(R) Cobalt-doped sodium borohydride, Sodium tetrahydridoborate Sodium tetrahydridoborate, VenPure(R) AF Sodiumborohydrideonneutralalumina Sodiumborohydridepellets NATRIUMBORANAT (MICROGRANULAT) SODIUM BOROHYDRIDE SOLUTION 30G/LT IN 1M NAOH Sodium borohydride, 99%, powder Sodium borohydride, (12-13 mm), pellets, 98% SODIUM BOROHYDRIDE, 12% SOLUTION IN 40% AQUEOUS SODIUM HYDROXIDE SOLUTION Sodium borohydride0.5 M solution in diglymeAcroSeal§3 Sodium borohydride12% solution in 40% aq. sodium hydroxide solution Sodium borohydride on silica gel Sodium borohydride,98%,granules, ca 3 mm SodiuM borohydride, (VenPure 20/20 solution), 20% aq. NaOH solution SodiuM borohydride, 99%, (VenPure SF powder), powder SodiuM borohydride, 99%, (VenPure AF caplets), caplets SODIUM BOROHYDRIDE FINE GRANULAR FOR SYN SODIUM BOROHYDRIDE GR FOR ANALYSIS Sodium borohydride, Sodium tetrahydridoborate

sodium borohydride

Chemoselective reductionAldehyde discriminationPharmaceutical intermediate synthesis

⚠ Attention: For research use only. Not for human or veterinary use.
Molecular FormulaBNa
Molecular Weight33.80 g/mol
Cat. No.B8817699
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Technical Parameters

Basic Identity
Product Name sodium borohydride
Molecular Formula BNa
Molecular Weight 33.80 g/mol
Structural Identifiers
SMILES [B-].[Na+]
InChI InChI=1S/B.Na/q-1;+1
InChIKey ODGROJYWQXFQOZ-UHFFFAOYSA-N
Commercial & Availability
Standard Pack Sizes 100 g / 500 g / 1 kg / 5 kg / Bulk Custom
Availability In Stock
Custom Synthesis Available on request

Sodium Borohydride Technical Specifications

Sodium borohydride (NaBH4, CAS 16940-66-2) is a white crystalline inorganic complex metal hydride with a molecular weight of 37.83 g/mol, widely employed as a selective reducing agent in pharmaceutical synthesis, fine chemical manufacturing, and laboratory research . It delivers four hydride equivalents per mole for the reduction of aldehydes and ketones to primary and secondary alcohols, respectively, while exhibiting negligible reactivity toward carboxylic acids, esters, amides, nitriles, and alkene double bonds under ambient conditions [1]. Commercial availability includes powder, granular, and pellet forms with standard purity specifications ranging from ≥98% (ACS/reagent grade) to 99% (high-purity industrial grade) .

▸Selective aldehyde/ketone reduction workflow
▸Preserves ester, amide, and nitrile functionalities
▸Compatible with water and ethanol solvents
▸Available in powder, granular, and pellet forms

Why Sodium Borohydride Cannot Be Substituted

Substituting sodium borohydride with alternative metal hydrides such as lithium aluminum hydride (LiAlH4), sodium cyanoborohydride (NaBH3CN), or sodium triacetoxyborohydride (STAB) without systematic evaluation introduces substantial risks to reaction selectivity, process safety, and economic viability. NaBH4’s moderate hydride reactivity enables chemoselective reduction of aldehydes and ketones while preserving ester, amide, nitrile, and carboxyl functional groups, a compatibility profile not shared by more potent reagents like LiAlH4, which reduces esters, amides, and carboxylic acids and reacts violently with protic solvents [1]. Furthermore, NaBH4’s tolerance for aqueous and alcoholic reaction media contrasts sharply with LiAlH4’s requirement for rigorously anhydrous conditions due to pyrophoric hazards and hydrogen evolution upon water contact [2]. At the opposite end of the reactivity spectrum, NaBH3CN and STAB exhibit attenuated reducing power optimized for reductive amination, rendering them insufficient for direct carbonyl-to-alcohol reductions where NaBH4 remains the agent of choice [3]. These divergent functional group compatibilities, solvent requirements, and safety profiles preclude generic interchange and necessitate evidence-driven reagent selection based on specific transformation objectives.

LiAlH4 may compromise functional group selectivityLiAlH4 reduces esters, amides, and nitriles; NaBH4 preserves them. Direct substitution may destroy sensitive groups.
Weaker borohydrides may not achieve direct carbonyl reductionNaBH3CN and STAB are optimized for reductive amination and often insufficient for aldehyde/ketone to alcohol conversion.
LiAlH4 requires rigorous anhydrous conditionsLiAlH4 reacts violently with water and alcohols, demanding specialized equipment; NaBH4 tolerates aqueous media for safer scale-up.

Sodium Borohydride Comparative Performance Evidence

Chemoselective Aldehyde Reduction Over Ketones

Sodium borohydride achieves >95% chemoselectivity for aldehyde reduction in the presence of ketones when conducted in 30% ethanol/dichloromethane at -78°C [1]. This selectivity is not attainable with stronger reducing agents such as LiAlH4, which indiscriminately reduces both aldehydes and ketones under all conditions, nor with LiBH4, which exhibits comparable but less predictable selectivity and is more costly for routine laboratory and industrial application.

Aldehyde vs Ketone Selectivity
Head-to-head
NaBH4: >95% selectivity for aldehyde
LiAlH4: 0% (both reduced)
Supports chemoselective aldehyde reduction workflow
30% EtOH/CH2Cl2, -78°C
Chemoselective reductionAldehyde discriminationPharmaceutical intermediate synthesis

Functional Group Compatibility vs LiAlH4

Under ambient conditions, NaBH4 selectively reduces aldehydes and ketones while leaving carboxylic acids, esters, amides, nitriles, and alkene double bonds unaffected [1]. In contrast, LiAlH4 reduces all aforementioned functional groups—carboxylic acids and esters to primary alcohols, amides to amines, nitriles to primary amines, and epoxides via ring-opening [2]. The practical consequence is that NaBH4 tolerates ester, amide, and nitrile functionalities, whereas LiAlH4 does not.

Functional Group Compatibility
Head-to-head
NaBH4: 2 carbonyls reduced, 5 groups preserved
LiAlH4: 7 groups reduced
Multi-step synthesis with ester/amide integrity
Ambient conditions, protic solvent compatible
Functional group toleranceChemoselectivityMulti-step synthesis

Solvent Compatibility vs LiAlH4

NaBH4 reductions are routinely conducted in water or ethanol as reaction solvents due to the reagent’s kinetic stability toward protic media [1]. LiAlH4, by contrast, reacts violently with water and alcohols, liberating hydrogen gas and requiring strictly anhydrous ethereal solvents (diethyl ether, THF) with rigorous exclusion of moisture [2]. Quantitative assessment of industrial practice confirms that NaBH4 is ‘often the agent of choice giving reasonable atom economy, good economics and ease of handling on scale’ whereas ‘more powerful reductants like LiAlH4 or Red-Al™ are rarely required for most ketones’ [3].

Solvent Compatibility
Head-to-head
NaBH4: water and ethanol compatible
LiAlH4: anhydrous ether only
Safer scale-up, lower solvent procurement costs
ACS GCI: often agent of choice for ketones
Process safetySolvent compatibilityIndustrial scale-up

Aqueous-Alkaline Solution Storage Stability

Aqueous-alkaline NaBH4 solutions undergo gradual decomposition via water interaction to form sodium tetrahydroxoborate, which precipitates as NaB(OH)4·2H2O [1]. Comparative analysis of freshly prepared solutions versus solutions stored for one year revealed decreasing NaBH4 content correlated with reduced extent of catalyst precursor reduction; however, the remaining active NaBH4 in aged solutions retained sufficient reducing capacity to generate active cobalt catalysts [2]. The increase in pH up to 13 during prolonged storage promotes cobalt hydroxide formation, which exhibits low hydrolytic activity [3].

Storage Stability (Aqueous-Alkaline)
Reported
Fresh: full reduction; 1-year stored: partial but sufficient catalyst activation
Informs pre-prepared solution procurement planning
Decomposition to NaB(OH)4; pH increase to 13
Solution stabilityStorage lifetimeCatalyst reduction

Chemo- and Regioselective Epoxide Reduction

Under standard conditions, NaBH4 does not reduce epoxides. However, in mixed solvent systems containing methanol (t-butyl alcohol–methanol or 1,2-dimethoxyethane–methanol), NaBH4 reduces mono- and gem-disubstituted epoxides to more substituted alcohols with yields ranging from 73% to 100% and regioselectivities from 89:11 to 100:0 [1]. Critically, this system exhibits excellent chemoselectivity, reducing epoxides selectively in the presence of carbamoyl, carboxyl, nitro, cyano, and bromo groups—functional groups that would be reduced or degraded by LiAlH4 [2].

Epoxide Reduction with Sensitive Groups
Cross-study comparable
Yield 73–100%; regioselectivity up to 100:0
Preserves carbamoyl, nitro, cyano, bromo groups
Epoxide ring-opening without protecting groups
MeOH mixed-solvent system required
Epoxide reductionRegioselectivityMixed solvent system

Sodium Borohydride Optimal Application Scenarios

Pharmaceutical Chemoselective Aldehyde Reduction

When a synthetic intermediate contains both aldehyde and ketone moieties and only the aldehyde requires reduction, NaBH4 in 30% ethanol/dichloromethane at -78°C achieves >95% chemoselectivity for aldehyde over ketone [1]. This scenario is common in steroid, prostaglandin, and macrolide antibiotic synthesis where multiple carbonyl groups coexist. Alternative reagents such as LiAlH4 reduce both functional groups indiscriminately, while LiBH4 offers inferior selectivity and higher cost. Procurement of NaBH4 eliminates the need for orthogonal protecting group strategies, reducing step count and improving overall yield.

Ester- and Amide-Compatible Carbonyl Reduction

In synthetic routes where an ester, amide, or nitrile group must remain intact during a ketone or aldehyde reduction step, NaBH4 is the only suitable common hydride reagent [1]. LiAlH4 would reduce these functionalities to alcohols or amines, necessitating costly and time-consuming protection-deprotection sequences. This differential functional group tolerance is documented across hundreds of pharmaceutical process patents, including the industrial production of fexofenadine where NaBH4 is employed for selective ketone reduction while preserving ester and amide integrity .

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    • CAS: 16940-66-2
    • Molecular Formula: BH4Na
    • MDL Number: MFCD00003518
    • Molecular Weight (g/mol): 37.83

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    • Boiling point: 500°C
    • Density: 1.035 g/mL at 25 °C
    • bulk density: 350-500kg/m3
    • Melting point: >300 °C (dec.) (lit.)

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    • CAS: 16940-66-2
    • Molecular Formula: BH4Na
    • MDL Number: MFCD00003518
    • Molecular Weight (g/mol): 37.83

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