373-52-4

Basic information

• Product Name: Bromofluoromethane
• Synonyms: BROMOFLUOROMETHANE-PYRIDINIUM ADDUCT;Bromofluoromethane 98%;Bromofluoromethane98%;BROMOFLUOROMETHANE-PYRIDINIUM ADDUCT: 99.8% (QUANTITIES PER ACTIVE INGREDIENT);Fluorobromomethane;Fluoromethyl bromide;BroMofluoroMethane [in solution or in cylinder (gas)];Methane, broMofluoro-(6CI,7CI,8CI,9CI)
• CAS NO: 373-52-4
• Molecular Formula: CH2BrF
• Molecular Weight: 112.93
• EINECS: 206-770-6
• Product Categories: Fluoro-containing compounds
• Mol File: 373-52-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 17-18°C
• Flash Point: None
• Appearance: Clear colourless to light yellow liquid
• Density: 1,76 g/cm3
• Vapor Pressure: 4860mmHg at 25°C
• Refractive Index: 1.3750 (estimate)
• CAS DataBase Reference: Bromofluoromethane(CAS DataBase Reference)
• NIST Chemistry Reference: Bromofluoromethane(373-52-4)
• EPA Substance Registry System: Bromofluoromethane(373-52-4)

Safety Data

• Hazard Codes: T
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• Hazardous Substances Data: 373-52-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

InChI:InChI=1/CH3F3Si/c1-5(2,3)4/h1H3

Synthetic route

dibromofluoromethane (1868-53-7) → bromofluoromethane (373-52-4)

Conditions	Yield
	53.1%
With sodium amalgam In water; isopropyl alcohol	50%

dibromofluoromethane (1868-53-7) → Methyl fluoride (593-53-3) + bromofluoromethane (373-52-4)

Conditions	Yield
With ethanol; zinc

halon-1211 (353-59-3) → bromodifluoromethane (1511-62-2) + Difluoromethane (75-10-5) + bromofluoromethane (373-52-4) + dichloromethane (75-09-2) + Chlorodifluoromethane (75-45-6) + 1,1-dibromomethane (74-95-3)

Conditions	Yield
With hydrogen In gas at 400 - 900℃; under 760 Torr; Rate constant; Product distribution; Mechanism; other reagents; Ea;

methane (34557-54-5) + Bromotrifluoromethane (75-63-8) → methyl bromide (74-83-9) + Vinyl bromide (593-60-2) + bromofluoromethane (373-52-4) + trifluoromethan (75-46-7) + Vinylidene fluoride (75-38-7) + 1,1-dibromomethane (74-95-3)

Conditions	Yield
Mn exchaged zeolite ZSM-5 at 599.85℃; Product distribution; other catalysts, temp.;

silver(I) monofluoroacetate (13126-91-5) → bromofluoromethane (373-52-4)

Conditions	Yield
With bromine at 20 - 80℃; for 1h; Bromination;
With bromine at 50 - 120℃; for 6h; Sealed tube;	1.4 g

silver-fluoroacetate → bromofluoromethane (373-52-4)

Conditions	Yield
With bromine

dibromofluoromethane (1868-53-7) + ethanol (64-17-5) + zinc → Methyl fluoride (593-53-3) + bromofluoromethane (373-52-4)

6α,9α-difluoro-17α-(furan-2-yl)carbonyloxy-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid (397864-40-3) + bromofluoromethane (373-52-4) → fluticasone furoate (397864-44-7)

Conditions	Yield
In butanone at 0 - 22℃;	99.3%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at -20℃;	88%
Stage #1: 6α,9α-difluoro-17α-(furan-2-yl)carbonyloxy-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid With sodium carbonate In N,N-dimethyl-formamide at -15 - -5℃; for 0.25h; Stage #2: bromofluoromethane In N,N-dimethyl-formamide at -15 - -5℃; for 3.3h;	79.08%

bromofluoromethane (373-52-4) + 4-bromobutyl thiophene-2-carboxylate → C10H13FO2S

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	97%

bromofluoromethane (373-52-4) + tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-3-methyl-4-(hydroxyimino) pyrrolidine-1-carboxylate (1356857-65-2) → tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-3-methyl-4-(fluoromethoxyimino)pyrrolidine-1-carboxylate (1356857-68-5)

Conditions	Yield
With sodium hydroxide In water; toluene at 20℃; Cooling;	96.1%

bromofluoromethane (373-52-4) + C11H11BrO4 → C12H13FO4

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	96%

bromofluoromethane (373-52-4) + 1-bromo-3,3-diphenylpropane (20017-68-9) → 4,4-diphenyl-1-fluorobutane

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	96%

bromofluoromethane (373-52-4) + tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate (175463-36-2) → tert-butyl 3-((tert-butoxycarbonylamino)methyl)-4-(fluoromethoxyimino)pyrrolidine-1-carboxylate (1356857-66-3)

Conditions	Yield
With sodium hydroxide In water; toluene at 0 - 20℃;	95%

bromofluoromethane (373-52-4) + (4-bromophenyl)(phenyl)methanone (90-90-4) → (4-(fluoromethyl)phenyl)(phenyl)methanone (64747-74-6)

Conditions	Yield
With nickel(II) iodide; dmap; manganese; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 40℃; for 24h; Sealed tube; Inert atmosphere;	95%

bromofluoromethane (373-52-4) + 9-bromophenanthrene (573-17-1) → 9-(fluoromethyl)phenanthrene

Conditions	Yield
With nickel(II) iodide; dmap; manganese; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 40℃; for 24h; Sealed tube; Inert atmosphere;	95%

bromofluoromethane (373-52-4) + 3-bromopropyl 2-(4-isobutylphenyl)propanoate → C17H25FO2

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	95%

1-(4-bromobutoxy)-4-(trifluoromethyl)benzene + bromofluoromethane (373-52-4) → C12H14F4O

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	95%

bromofluoromethane (373-52-4) + tert-butyl 3-cyanoazetidine-1-carboxylate (142253-54-1) → tert-butyl 3-cyano-3-(fluoromethyl)azetidine-1-carboxylate (1228581-11-0)

Conditions	Yield
Stage #1: tert-butyl 3-cyanoazetidine-1-carboxylate With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: bromofluoromethane In tetrahydrofuran at -78 - 25℃; for 16.5h; Stage #3: With ammonium chloride In tetrahydrofuran; water at 0℃;	94%

(S)-tert-butyl 1-(7-hydroxy-2,3-dihydro-1H-pyrrolo-[1,2-a]indol-9-yl)propan-2-ylcarbamate (439948-95-5) + bromofluoromethane (373-52-4) → (S)-tert-butyl 1-[7-(fluoromethoxy)-2,3-dihydro-1H-pyrrolo-[1,2-a]indol-9-yl]propan-2-ylcarbamate

Conditions	Yield
Stage #1: (S)-tert-butyl 1-(7-hydroxy-2,3-dihydro-1H-pyrrolo-[1,2-a]indol-9-yl)propan-2-ylcarbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: bromofluoromethane In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;	94%

3-(benzyloxy)phenyl bromide (53087-13-1) + bromofluoromethane (373-52-4) → 1-(benzyloxy)-3-(fluoromethyl)benzene

Conditions	Yield
With nickel(II) iodide; dmap; manganese; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 40℃; for 24h; Sealed tube; Inert atmosphere;	94%

bromofluoromethane (373-52-4) + 1-Bromo-3-phenylpropane (637-59-2) → 4-fluoro-1-phenylbutane (909912-96-5)

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Sealed tube; Glovebox;	94%

bromofluoromethane (373-52-4) + C11H13BrO3 → C12H15FO3

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	94%

9-(3-bromophenyl)carbazole (185112-61-2) + bromofluoromethane (373-52-4) → 9-(3-(fluoromethyl)phenyl)-9H-carbazole

Conditions	Yield
With nickel(II) iodide; dmap; manganese; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 40℃; for 24h; Sealed tube; Inert atmosphere;	93%

3-bromodibenzofuran (26608-06-0) + bromofluoromethane (373-52-4) → 3-(fluoromethyl)dibenzo[b,d]furan

Conditions	Yield
With nickel(II) iodide; dmap; manganese; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 40℃; for 24h; Sealed tube; Inert atmosphere;	93%

bromofluoromethane (373-52-4) + 4-<(4-bromobutyl)oxy>-3-methoxybenzaldehyde (3439-71-2) → C13H17FO3

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	93%

bromofluoromethane (373-52-4) + 1-[(3-bromopropoxy)methyl]-benzene (54314-84-0) → 1-benzyloxy-4-fluorobutane

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	93%

bromofluoromethane (373-52-4) + 3-bromopropyl 1-naphthoate → C15H15FO2

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	93%

bromofluoromethane (373-52-4) + C8H9BrO3 → C9H11FO3

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	93%

bromofluoromethane (373-52-4) + C18H27BrO3 → C19H29FO3

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	92%

bromofluoromethane (373-52-4) + C18H23BrO3 → C19H25FO3

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	92%

bromofluoromethane (373-52-4) + 3-phenoxypropyl bromide (588-63-6) → (4-fluorobutoxy)benzene (70659-95-9)

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	92%

bromofluoromethane (373-52-4) + C10H6BrF5O2 → C11H8F6O2

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	92%

bromofluoromethane (373-52-4) + C13H14BrNO2 → C14H16FNO2

Conditions	Yield
With nickel(II) bromide dimethoxyethane; C9H11N3; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	92%

bromofluoromethane (373-52-4) + 17-propionate carbothioic acid (80474-45-9) → flixotide (80474-14-2)

Conditions	Yield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at -10 - 20℃; for 2h;	91.7%
With potassium carbonate In acetone at -5 - 0℃; for 2 - 5h; Product distribution / selectivity;	84.51%
Stage #1: 17-propionate carbothioic acid With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: bromofluoromethane In acetone at 0 - 5℃;	80%

bromofluoromethane (373-52-4) + C26H28F2O6S → fluticasone furoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at -10 - 0℃; for 16h; Inert atmosphere;	91.12%

bromofluoromethane (373-52-4) + 4-biphenylboronic acid (5122-94-1) → 4-(fluoromethyl)-1,1‘-biphenyl

Conditions	Yield
With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate In 1,4-dioxane at 70℃; for 12h; Reagent/catalyst; Solvent; Concentration; Suzuki Coupling;	91%
With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate In 1,4-dioxane; 1,2-dimethoxyethane at 70℃; for 24h; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere;	90%

bromofluoromethane (373-52-4) + 4-iodo-biphenyl (1591-31-7) → 4-(fluoromethyl)-1,1‘-biphenyl

Conditions	Yield
With pyridine-4-carbonitrile; nickel(II) iodide; manganese; 4,4'-dimethyl-2,2'-bipyridines In N,N-dimethyl acetamide at 40℃; for 24h; Inert atmosphere; Sealed tube;	91%

Upstream product

• 353-59-3 halon-1211 
• 34557-54-5 methane 
• 75-63-8 Bromotrifluoromethane 
• 1868-53-7 dibromofluoromethane 
• 64-17-5 ethanol 
• 13126-91-5 silver(I) monofluoroacetate 

Downstream Products

• 80474-14-2 flixotide 
• 688032-49-7 17α-(cyclohexylmethylcarbonyl)oxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid S-fluoromethyl ester 
• 326-49-8 benzoic acid-(4-fluoro-butyl ester) 
• 1120341-47-0 (5-fluoropentyl)benzene 

Relevant articles and documents

The vibrational spectra and normal coordinates analysis of bromofluoromethane, CH2BrF

The infrared gas-phase spectra of bromofluoromethane (CH2BrF) have been studied in the region below 6200 cm-1 under conditions of medium resolution. All the fundamentals and many overtones, combination and hot bands have been assigned leading to an almost complete set of anharmonicity constants. Rotational analyses have been performed on the observed Q-branch features of over 10 bands. Enriched 79Br and 81Br samples were also employed to confirm vibrational assignment and supply further data. Analyses of Fermi resonance are made. The molecular structure was calculated ab initio at the Hartree-Fock (HF), the second-order Moller-Plesset (MP2) and the density functional theory (DFT) level with the 6M311++G(3df, 2pd) basis set. The ab initio force constants obtained from the vibrational analysis at B3LYP/6-311++G(3df, 2pd) level of theory were employed to fit the experimental data and an optimal harmonic force field was obtained for the CH2BrF molecule. (C) 2000 Elsevier Science B.V.

Catalytic reaction of methane with CBrF3

The catalytic reaction of CH4 with CBrF3 over Co, Cu and Mn ZSM-5 zeolites is described; major products (at low temperatures) are those expected for simple hydrodebromination: CH3Br and CHF3.

Process for the preparation of bromofluoromethane

A method for the preparation of bromofluoromethane by reducing dibromofluoromethane in the presence of mercury.