Buy Trifluoronitrosomethane Cas 334-99-6

Buy Trifluoronitrosomethane Cas 334-99-6

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Buy Trifluoronitrosomethane Cas 334-99-6

Buy Trifluoronitrosomethane Cas 334-99-6

Trifluoronitrosomethane (commonly abbreviated as TFNM) is a toxic and unstable gaseous compound consisting of a trifluoromethyl group covalently bound to a nitroso group. The gas is notable for its intense blue colour. Buy Trifluoronitrosomethane Cas 334-99-6

 

Trifluoronitrosomethane

Reaction KineticsRadical ChemistryNOx Scavenging

Sourcing a stable, monomeric CF₃NO reagent for nitric oxide studies or radical generation often fails with nitrosomethane (rapid dimerization) or CF₃I (lacks the nitroso moiety). Trifluoronitrosomethane (TFNM) overcomes these barriers: Buy Trifluoronitrosomethane Cas 334-99-6

• Monomeric stability via the electron-withdrawing CF₃ group; no spontaneous dimerization.

• 100-fold slower reaction with NO relative to CH₃NO, enabling accurate kinetic deconvolution of NOx networks.

• Enables clean condensation with hydroxylamines to access N-trifluoromethyl-N-nitroso intermediates for prodrug discovery. Buy Trifluoronitrosomethane Cas 334-99-6

• Prepared on-demand by UV-driven CF₃I/NO synthesis (≤90% yield), ensuring reliable supply.

• ≥95% purity, shipped globally for immediate research use. Buy Trifluoronitrosomethane Cas 334-99-6

Conventional nitrosoalkanes dimerize rapidly, preventing precise metering. Trifluoronitrosomethane (CF3NO) remains a stable monomeric blue gas, enabling continuous flow processing. It co-polymerizes 1:1 with TFE to form chemically resistant nitroso rubber seals, performs ene reactions at -78 °C for N-trifluoromethylhydroxylamine installation, and traps radicals with large 19F hyperfine coupling constants. Supplied as ca. 0.5 M solution in DCM. Buy Trifluoronitrosomethane Cas 334-99-6

CAS Number

334-99-6

Product Name

Trifluoronitrosomethane

IUPAC Name

trifluoro(nitroso)methane

Molecular Formula

CF3NO

Molecular Weight

99.012 g/mol

InChI

InChI=1S/CF3NO/c2-1(3,4)5-6

InChI Key

PGOMVYSURVZIIW-UHFFFAOYSA-N

SMILES

C(N=O)(F)(F)F

Canonical SMILES

C(N=O)(F)(F)F

Synonyms

Trifluoronitrosomethane, Trifluoro(nitroso)methane, Nitrosotrifluoromethane, CF3NO

Purity

≥95%

Package Size

5 ml, 10 ml, 25 ml

Trifluoronitrosomethane Procurement Overview

Trifluoronitrosomethane (CF3NO) is a highly reactive, intense blue gas characterized by the rare combination of a strongly electron-withdrawing trifluoromethyl group and a nitroso moiety [1]. Unlike many aliphatic nitroso compounds, it exists as a stable monomer at room temperature, making it a highly processable gaseous reagent for continuous flow systems . In industrial and advanced laboratory settings, CF3NO is primarily procured as an essential comonomer for the synthesis of highly chemically resistant nitroso rubbers (copolymers with tetrafluoroethylene), as a highly electrophilic enophile for ultra-low-temperature ene reactions, and as a precursor for stable nitroxide spin traps and trifluoromethylating agents[2]. Its unique electronic structure dictates its selection over non-fluorinated or fully oxidized analogs in demanding synthetic and materials science workflows. Buy Trifluoronitrosomethane Cas 334-99-6

Research Fit

Monomeric formEnsures consistent stoichiometry in radical trapping and photochemical workflows
Fluorinated electrophilicitySupports selective condensation with hydroxylamines and controlled nitroxide generation Buy Trifluoronitrosomethane Cas 334-99-6
Low-barrier C–N cleavageSupports CF₃ radical generation under mild experimental conditions

References

Why Substitution Fails for Trifluoronitrosomethane

Substituting Trifluoronitrosomethane with non-fluorinated aliphatic analogs, such as nitrosomethane (CH3NO), results in immediate process failure because CH3NO is kinetically unstable and rapidly dimerizes to an azodioxide, requiring cumbersome in situ generation [1]. The strong electron-withdrawing nature of the CF3 group in CF3NO prevents this dimerization, allowing it to be metered precisely as a stable monomeric gas . Furthermore, attempting to use alternative fluorinated monomers (like hexafluoropropylene) in elastomer polymerization fails to yield the unique -N(CF3)-O- backbone required for nitroso rubbers; these specialty materials rely entirely on CF3NO’s specific alternating copolymerization behavior with tetrafluoroethylene to achieve their signature extreme chemical resistance and low-temperature flexibility [2]. Buy Trifluoronitrosomethane Cas 334-99-6

Substitution Risk

CH₃NO substitution
Nitrosomethane dimerizes at room temperature, altering stoichiometry; its reaction kinetics with NO differ substantially from CF₃NO, invalidating kinetic models built on CF₃NO data
CF₃I substitution
Trifluoroiodomethane lacks the nitroso moiety required for alkene or amine reactions that proceed via radical nitroxide intermediates, leading to fundamentally different product distributions

References

Quantitative Evidence for Trifluoronitrosomethane

Kinetic Stabilization Against Dimerization

A primary procurement advantage of CF3NO is its existence as a stable, meterable gas at room temperature, contrasting sharply with unfluorinated aliphatic nitroso compounds [1]. While nitrosomethane (CH3NO) rapidly dimerizes to its azodioxide form, complicating direct stoichiometric dosing, CF3NO remains kinetically stabilized as a monomeric species due to the strong inductive effect of the trifluoromethyl group . This allows for direct mass-flow control in continuous synthesis or polymerization reactors. Buy Trifluoronitrosomethane Cas 334-99-6

Evidence Dimension Monomer-dimer equilibrium state at 25 °C
Target Compound Data >99% stable monomeric gas (CF3NO)
Comparator Or Baseline Rapidly dimerizing solid/liquid azodioxide (CH3NO)
Quantified Difference Complete elimination of the dimerization pathway, enabling direct gas-phase handling.
Conditions Standard temperature and pressure (25 °C, 1 atm)

Eliminates the need for thermal cracking of dimers or complex in situ generation, streamlining industrial gas dosing and reactor design.

NO Reaction Kinetics
Reported
k = 17.4 exp(–1110 K/T) dm⁶ mol⁻² s⁻¹
~100× slower reaction vs CH₃NO at room temperature
Supports kinetic model differentiation from non-fluorinated analogs
Gas-phase, third-order: CF₃NO + 2NO

Ultra-Low Temperature Enophilicity

CF3NO exhibits exceptional reactivity as an enophile, enabling the functionalization of unactivated olefins under extremely mild conditions [1]. In comparative synthetic workflows, standard nitrosoarenes often require elevated temperatures to undergo ene reactions, which can degrade sensitive substrates. In contrast, CF3NO reacts rapidly with alkenes such as propene and isobutene at temperatures as low as -78 °C to form N-alkenyl-N-trifluoromethylhydroxylamines [1]. The nitrogen atom selectively bonds to the least substituted carbon, providing high regiocontrol. Buy Trifluoronitrosomethane Cas 334-99-6

Evidence Dimension Minimum effective reaction temperature for ene addition
Target Compound Data Rapid reaction at -78 °C (CF3NO)
Comparator Or Baseline Requires room temperature or heating (Standard nitrosoarenes)
Quantified Difference An approximately 100 °C reduction in required activation temperature for ene functionalization.
Conditions Reaction with simple unactivated olefins (e.g., propene) in inert solvent

Allows chemists to functionalize thermally sensitive complex molecules or highly volatile olefins without yield-destroying side reactions.

Monomeric Stability
Reported
CF₃NO
Stable monomer at room temperature
CH₃NO
Undergoes dimerization at room temperature
Supports consistent stoichiometry and avoids dimer-derived impurities
Room temperature, gas phase, absence of NO

Alternating Copolymerization with TFE

In the production of specialty elastomers, CF3NO is irreplaceable due to its unique copolymerization dynamics with tetrafluoroethylene (TFE) [1]. Unlike traditional fluoromonomers that form random carbon-carbon backbones, CF3NO acts as a diradical trap, strictly alternating with TFE to form a -[N(CF3)-O-CF2-CF2]- backbone [1]. This 1:1 alternating structure is responsible for the resulting nitroso rubber’s absolute non-flammability and resistance to strong oxidizers like nitrogen tetroxide. Buy Trifluoronitrosomethane Cas 334-99-6

Evidence Dimension Polymer backbone structure and monomer sequence
Target Compound Data Strictly 1:1 alternating N-O-C-C backbone (CF3NO + TFE)
Comparator Or Baseline Random C-C backbone (Hexafluoropropylene + TFE)
Quantified Difference Yields a 100% alternating heteroatom-rich backbone, whereas standard fluoromonomers yield random carbon-only backbones.
Conditions Radical or coordination-catalyzed copolymerization

Essential for manufacturing specialized seals and gaskets used in aerospace and military applications involving hypergolic propellants. Buy Trifluoronitrosomethane Cas 334-99-6

C–N Bond Length
Class-level
r(C–N) = 1.555 ± 0.015 Å
~6% elongated vs typical amine C–N bond (~1.47 Å)
Supports homolytic cleavage studies for CF₃ radical generation
Gas-phase electron diffraction

Nitroxide Stability in Spin Trapping

When utilized as a spin trap in Electron Spin Resonance (ESR) spectroscopy, CF3NO offers distinct advantages over conventional traps like 2-methyl-2-nitrosopropane (MNP) [1]. The incorporation of the trifluoromethyl group yields nitroxide radicals with highly resolved ESR spectra featuring large 19F and 14N hyperfine coupling constants[1]. Furthermore, the strong electron-withdrawing nature of the CF3 group stabilizes the resulting nitroxide adducts against disproportionation, significantly extending their half-lives in complex matrices. Buy Trifluoronitrosomethane Cas 334-99-6

Evidence Dimension Spin adduct spectral resolution and kinetic stability
Target Compound Data Highly stable nitroxides with distinct 19F/14N hyperfine splitting (CF3NO adducts)
Comparator Or Baseline Faster disproportionation and overlapping signals (MNP adducts)
Quantified Difference Provides distinct 19F multiplet splitting and prevents rapid disproportionation seen in standard alkyl nitroxides.
Conditions ESR spin trapping of transient alkyl or oxygen-centered radicals

Provides analytical chemists with a more robust tool for detecting and quantifying short-lived radical intermediates in reaction mechanisms or biological models. Buy Trifluoronitrosomethane Cas 334-99-6

Surface Photolysis
Context-dependent
Matrix isolation

Photolysis quenched on alkali halide films; proceeds on argon films
Surface-dependent process design requires substrate-specific review
NaCl, NaBr, KCl, KBr at 10–100 K; 600–700 nm irradiation
Synthetic Yield
Reported
Photochemical route
Up to 90% yield
Thermal pyrolysis
~59% yield
Supports procurement and scale-up review for multigram preparation
CF₃I + NO, UV irradiation, ambient pressure
Vaporization Enthalpy
Reported
ΔvapH = 17.1 kJ/mol (at 159 K)
~30% lower vs CF₃NO₂ (est. 23–25 kJ/mol)
Supports cryogenic handling and low-temperature gas-phase workflows
NIST Standard Reference Data

Trifluoronitrosomethane Application Scenarios

Aerospace Nitroso Rubber Manufacture

Directly utilizing its 1:1 alternating copolymerization with TFE to produce chemically inert, non-flammable seals for hypergolic propellant systems[1].

Low-Temperature Olefin Functionalization

Employing its extreme enophilicity at -78 °C to introduce N-trifluoromethylhydroxylamine groups into complex, thermally sensitive organic molecules via ene reactions [2].

ESR Spin Trapping Workflows

Using CF3NO to capture transient radical species, leveraging the large 19F hyperfine coupling constants to unambiguously identify radical structures in mechanistic studies [3].

Synthesis of Trifluoromethylating Agents

Acting as a core precursor to generate reagents like N-trifluoromethyl-N-nitrosotrifluoromethanesulfonamide (TNS-Tf), which are used for the electrophilic trifluoromethylation of aromatics and thiols [4].

Application Fit Matrix

Application
Selection Property
Validation Focus
Controlled NOx scavenging studies
Differentiated kinetics from non-fluorinated nitrosoalkanes
Reaction rate under experimental NOx conditions
N-Trifluoromethyl-N-nitroso derivative synthesis
Monomeric electrophilic nitroso group
Condensation efficiency with target hydroxylamines
Matrix-isolation photochemistry
Surface-dependent photolysis behavior
Radical generation yield on target substrate films
On-demand laboratory synthesis
High-yield photochemical route from CF₃I and NO
Yield and purity under local UV setup

References

Trifluoronitrosomethane is a chemical compound with the molecular formula CF3N. It is classified as a nitroso compound, characterized by the presence of a nitroso group (−NO) attached to a carbon atom that is also bonded to three fluorine atoms. This unique structure imparts distinctive properties and reactivity patterns to trifluoronitrosomethane, making it an interesting subject of study in organic and inorganic chemistry. Buy Trifluoronitrosomethane Cas 334-99-6

Synthesis Analysis

Methods of Synthesis

Trifluoronitrosomethane can be synthesized through various methods, primarily involving the reaction of trifluoromethyl compounds with nitrous oxide or other nitrogen-containing reagents. One common method involves the following steps:

  1. Starting Materials: The synthesis typically begins with trifluoromethyl iodide or trifluoromethyl sulfonate as the precursor.
  2. Nitrosation Reaction: The precursor is treated with nitrous oxide in the presence of a suitable catalyst, often at elevated temperatures to facilitate the reaction.
  3. Purification: The resulting trifluoronitrosomethane is purified through distillation or chromatography to remove unreacted materials and byproducts.

Technical details regarding specific catalysts and reaction conditions can vary, but the fundamental approach remains consistent across different studies. Buy Trifluoronitrosomethane Cas 334-99-6

Molecular Structure Analysis

Structure and Data

Trifluoronitrosomethane has a simple yet significant molecular structure. The compound features:

  • Central Carbon Atom: The carbon atom is bonded to three fluorine atoms.
  • Nitroso Group: The nitroso group is directly attached to the carbon atom, contributing to the compound’s reactivity.

The molecular geometry around the carbon atom is tetrahedral due to the presence of three fluorine atoms and one nitrogen atom, which influences its chemical behavior. The bond angles are approximately 109.5∘, consistent with tetrahedral geometry.

Molecular Weight

The molecular weight of trifluoronitrosomethane is calculated as follows:

Molecular Weight=12.01 (C)+3×18.998 (F)+14.01 (N)=65.036 g mol
Chemical Reactions Analysis

Reactions and Technical Details

Trifluoronitrosomethane participates in various chemical reactions typical of nitroso compounds. Key reactions include:

  1. Nucleophilic Substitution: Trifluoronitrosomethane can undergo nucleophilic substitution reactions where nucleophiles attack the carbon atom, leading to the formation of new compounds.
  2. Reduction Reactions: Under reducing conditions, trifluoronitrosomethane can be converted into other derivatives, such as amines or difluoromethyl compounds.
  3. Decomposition: The compound can decompose under certain conditions, releasing nitrogen oxides and forming other byproducts.

The specific pathways and products depend on the reaction conditions such as temperature, pressure, and the presence of solvents or catalysts.

Mechanism of Action

Process and Data

The mechanism of action for trifluoronitrosomethane primarily involves its reactivity as a nitrating agent in organic synthesis. When it reacts with nucleophiles:

  1. Formation of Intermediate: A tetrahedral intermediate is formed when a nucleophile attacks the carbon atom.
  2. Elimination Step: This intermediate can then undergo elimination to release fluoride ions and form a new product.

This mechanism highlights the electrophilic nature of trifluoronitrosomethane due to the strong electronegativity of fluorine atoms surrounding the carbon center.

Physical and Chemical Properties Analysis

Physical Properties

  • Appearance: Trifluoronitrosomethane is typically a colorless gas or liquid at room temperature.
  • Boiling Point: The boiling point is approximately −10∘C.
  • Density: The density varies depending on its state (gas or liquid), but it is generally denser than air.

Chemical Properties

  • Stability: Trifluoronitrosomethane is relatively stable under standard conditions but can decompose under heat or light.
  • Reactivity: It exhibits high reactivity due to the presence of fluorine atoms and the nitroso group, making it useful in various chemical syntheses.
Applications

Scientific Uses

Trifluoronitrosomethane finds applications in several scientific fields:

  1. Organic Synthesis: It serves as an important reagent in organic synthesis for introducing trifluoromethyl groups into organic molecules.
  2. Material Science: Its unique properties make it valuable in developing new materials with specific thermal or chemical resistance.
  3. Pharmaceutical Chemistry: Trifluoronitrosomethane can be utilized in drug development processes where fluorinated compounds are desirable for enhancing biological activity.

Properties

CAS Number

334-99-6

Product Name

Trifluoronitrosomethane

IUPAC Name

trifluoro(nitroso)methane

Molecular Formula

CF3NO

Molecular Weight

99.012 g/mol

InChI

InChI=1S/CF3NO/c2-1(3,4)5-6

InChI Key

PGOMVYSURVZIIW-UHFFFAOYSA-N

SMILES

C(N=O)(F)(F)F

Canonical SMILES

C(N=O)(F)(F)F

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Properties

Although it is somewhat more kinetically stable than expected due to its fluorine substituents, trifluoronitrosomethane, like other nitroso compounds, has a C–N bond that is weaker than normal. The bond enthalpy of the C–N bond is only 167 kJ/mol (39.9 kcal/mol).[2]

Production

Trifluoronitrosomethane can be produced from the reaction of trifluoroiodomethane and nitric oxide under a UV light with a yield of up to 90%. A significant amount of mercury metal is needed to quench the iodine and nitrogen dioxide gases produced during the reaction.[3][4]

Pyrolysis of trifluoroacetyl nitrite gives trifluoronitrosomethane with yields over 85%. Carbon dioxide is formed as a side product. This method may also be employed to make other perfluoronitrosoalkanes from the corresponding perfluorocarboxylic acids.[5]

CF3C(O)ONO → CF3NO + CO2

History

Trifluoronitrosomethane was synthesised for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau.[6] It was formed through a reaction involving the fluorination of silver cyanide in the presence of silver nitrate and silver oxide.

 

Trifluoronitrosomethane: Compound Overview

Trifluoronitrosomethane (TFNM) is a toxic, deep-blue gas consisting of a trifluoromethyl group covalently bonded to a nitroso group [1]. Unlike the more common nitrosomethane (CH₃NO), TFNM is monomeric and kinetically stabilized by the electron-withdrawing effect of the three fluorine substituents, yet it retains a weak C–N bond (bond enthalpy: 39.9 kcal/mol) that underpins its unique reactivity profile [2]. This combination of fluorinated electrophilicity and latent nitroxide-generating capacity makes TFNM a distinct synthetic reagent rather than a mere analog of perfluoroalkyl iodides or non-fluorinated nitrosoalkanes.

R
Workflow
Fluorinated radical precursor and nitroso transfer reagent
S
Selection Logic
Monomeric gas-phase stability, controlled electrophilic reactivity
U
Use Context
Kinetic probe, photochemical synthesis, matrix isolation studies

Why Trifluoronitrosomethane Cannot Be Replaced

Attempting to replace trifluoronitrosomethane (CF₃NO) with structurally similar nitrosomethane (CH₃NO) or alternative CF₃-sources like trifluoroiodomethane (CF₃I) leads to fundamentally different experimental outcomes. Nitrosomethane spontaneously dimerizes and exhibits a reaction rate with nitric oxide that is two orders of magnitude faster, invalidating kinetic models based on CF₃NO data [1]. Conversely, CF₃I lacks the nitroso moiety required for reactions with alkenes or amines that proceed via radical nitroxide intermediates [2]. The quantitative differences documented below underscore that TFNM occupies a unique and non-interchangeable niche in synthetic and mechanistic chemistry.

Fluorine is the most electronegative element in the periodic table, and the fluorine atom has a small atomic radius, so fluorine-containing organic compounds have many wonderful properties. For example, the introduction of fluorine atoms or fluorine-containing groups into drug molecules can improve the permeability to cell membranes, metabolic stability and bioavailability; in addition, the introduction of fluorine atoms will improve the lipid solubility of the compound and promote its absorption in the body. The speed of delivery changes the physiological effect. In the field of medicinal chemistry, the introduction of fluorine atoms into organic molecules is an important direction for the development of new anticancer drugs, antitumor drugs, antiviral agents, anti-inflammatory drugs, and central nervous system drugs.

Target Reagent
Trifluoronitrosomethane (CF₃NO)
Monomeric, weak C–N bond, kinetically stabilized for controlled radical generation.
Common Substitute
Nitrosomethane (CH₃NO)
Spontaneous dimerization and ~100× faster NO reaction rate may invalidate kinetic models.
Target Reagent
Trifluoronitrosomethane (CF₃NO)
Contains electrophilic nitroso group for radical nitroxide intermediate pathways.
Common Substitute
Trifluoroiodomethane (CF₃I)
Lacks the nitroso moiety; cannot participate in alkene/amine reactions requiring –NO transfer.

Trifluoronitrosomethane: Kinetic and Structural Evidence

Nitric Oxide Reaction Kinetics

In a direct comparative kinetic study, the third-order reaction of trifluoronitrosomethane (CF₃NO) with nitric oxide (NO) was found to be approximately one hundred times slower at room temperature than the corresponding reaction of nitrosomethane (CH₃NO) [1]. The Arrhenius expression for CF₃NO was determined as k = 17.4 exp(–1110 K/T) dm⁶ mol⁻² s⁻¹, whereas the CH₃NO reaction was too fast for precise rate determination under identical conditions, highlighting a profound substituent effect on reactivity [1].

NO Reaction Kinetics
Head-to-head
~100× slower rate vs. CH₃NO
Supports controlled NOx scavenging workflow.
Third-order gas-phase kinetics, room temperature.
Reaction KineticsRadical ChemistryNOx Scavenging

Monomeric Stability at Room Temperature

Under identical experimental conditions (room temperature, absence of NO), trifluoronitrosomethane exists exclusively as the monomeric species, whereas nitrosomethane undergoes spontaneous dimerization [1]. This behavioral dichotomy is directly linked to the electron-withdrawing fluorine atoms, which kinetically stabilize the CF₃NO monomer despite a similarly weak C–N bond (bond enthalpy: 39.9 kcal/mol for CF₃NO [2] compared to typical nitroso C–N bond strengths).

Monomeric Stability
Head-to-head
Stable monomer vs. CH₃NO dimerization
Ensures consistent radical trapping stoichiometry.
Room temperature, gas phase, absence of NO.
Gas-Phase StabilityDimerization ThermodynamicsStructural Chemistry

C–N Bond Length and Polarization

Gas-phase electron diffraction reveals that the C–N bond in trifluoronitrosomethane is significantly elongated (r(C–N) = 1.555 ± 0.015 Å) [1] compared to the typical C–N single bond length in amines (~1.47 Å) [1]. This elongation, along with a contracted C–F bond (1.321 ± 0.004 Å), indicates substantial charge shift toward the fluorine atoms, rendering the nitroso group more electrophilic than in non-fluorinated analogs [1].

C–N Bond Length
Class-level
1.555 ± 0.015 Å (~6% elongation)
Predictable homolytic cleavage for CF₃ radical generation.
Gas-phase electron diffraction data.
Molecular StructureElectron DiffractionBond Polarization

Surface-Mediated Photolysis Quenching

While trifluoronitrosomethane photolyzes readily in the gas phase upon exposure to 600–700 nm light, adsorption onto alkali halide films (NaCl, NaBr, KCl, KBr) at 10–100 K completely quenches the photolysis process [1]. In contrast, photolysis proceeds normally on argon films, demonstrating that vibrational relaxation via surface phonons is the dominant quenching mechanism [1]. This environment-dependent behavior is not observed for simpler nitroso compounds like nitrosomethane, which decompose via different pathways.

Surface Photolysis
Supporting evidence
Quenched on alkali halide films at 10–100 K

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