598-73-2

Basic information

• Product Name: BROMOTRIFLUOROETHYLENE
• Synonyms: BROMOTRIFLUOROETHYLENE;BROMOTRIFLUOROETHYLENE MONOMER;Trifiuorobromoethylene;bromotrifluoro-ethen;Bromotrifluoroethene;bromotrifluoro-Ethene;bromotrifluoro-ethylen;C2BrF3
• CAS NO: 598-73-2
• Molecular Formula: C₂BrF₃
• Molecular Weight: 160.92
• EINECS: 209-948-1
• Mol File: 598-73-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: -2°C
• Flash Point: °C
• Appearance: /
• Density: 1,86 g/cm3
• Refractive Index: 1.3750 (estimate)
• CAS DataBase Reference: BROMOTRIFLUOROETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: BROMOTRIFLUOROETHYLENE(598-73-2)
• EPA Substance Registry System: BROMOTRIFLUOROETHYLENE(598-73-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11
• Safety Statements: 16-33
• RIDADR: 2419
• TSCA: T
• HazardClass: 2.1
• Hazardous Substances Data: 598-73-2(Hazardous Substances Data)

Usage

General Description

A colorless gas (boiling point -2 to 0°C) shipped in cylinders or, if polymerized, a liquid. Heating the containers of gas may cause them to rupture violently and rocket. Polymeric BROMOTRIFLUOROETHYLENE is a clear oily liquid of widely variable viscosity and density.

Air & Water Reactions

Highly flammable (gas).

Reactivity Profile

Reactivity often inhibited by adding tributylamine [Lancaster].

Health Hazard

Vapors may cause dizziness or asphyxiation without warning. Some may be toxic if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases.

Fire Hazard

EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Silane will ignite spontaneously in air. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

Safety Profile

A poison. A flammable gas. Iptes spontaneously in air. Incompatible with powerful oxidmers, O2. When heated to decomposition it emits highly toxic fumes of Br-, F-, and COCF2

InChI:InChI=1/C2BrF3/c3-1(4)2(5)6

Synthetic route

1,2-dibromo-1,1,2-trifluoroethane (354-04-1) → 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide
With potassium hydroxide; water at 76℃;
With pyrographite; potassium nitrate at 20 - 400℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;

2-bromo-1,1,1-trifluoroethane (421-06-7) → 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
Irradiation; radiation > 237 nm;

3-bromo-3-(trifluoromethyl)diazirine (117113-33-4) → 2-bromo-1,1,1-trifluoroethane (421-06-7) + 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
Irradiation;
Irradiation; radiation > 330 nm;

1,2-dibromo-1,1-difluoroethane (75-82-1) + AgF → 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
at 120℃;

trifluorodibromoethane → 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
With ethanol; potassium acetate; potassium carbonate
With sodium ethanolate

(pentafluoro ethyl) magnesiumbromide (56184-59-9) → 1,1-dibromo-2,2-difluoroethylene (430-85-3) + 1-bromo-1,2,2-trifluoroethene (598-73-2) + Iodotrifluoroethylene (359-37-5)

Conditions	Yield
In diethyl ether thermal decompn. on warming from -40°C to 20°C;
In diethyl ether thermal decompn. on warming from -40°C to 20°C;

(1,2-dibromotrifluoroethyl)pentafluorosulfur(VI) (22687-88-3) → fluorosulfonyl fluoride (640723-20-2, 2699-79-8, 12769-73-2) + 1-bromo-1,2,2-trifluoroethene (598-73-2) + (trifluoroethenyl)pentafluorosulfur(VI) (1186-51-2)

Conditions	Yield
With Cu with Cu powder, 188°C;

N(C4H9)4(1+)*CF2CFBF3(1-)=N(C4H9)4[CF2CFBF3] (1375484-85-7) → 1-bromo-1,2,2-trifluoroethene (598-73-2) + [Bu4N][CF2BrCFBrBF3] (1375485-13-4)

Conditions	Yield
With bromine In dichloromethane at 20℃; for 66h;

N(C4H9)4(1+)*CF2CFBF3(1-)=N(C4H9)4[CF2CFBF3] (1375484-85-7) → bromopentafluoroethane (354-55-2) + 1-bromo-1,2,2-trifluoroethene (598-73-2)

Conditions	Yield
With bromine trifluoride; bromine In 1,1,1,3,3-pentafluorobutane at -15℃; for 0.25h;

polytetrafluoroethylene (116-14-3) → 1-bromo-1,2,2-trifluoroethene (598-73-2) + hexafluoro-1,3-butadiene (685-63-2)

Conditions	Yield
Stage #1: polytetrafluoroethylene With magnesium; zinc(II) chloride at 60℃; under 3800.26 Torr; Inert atmosphere; Autoclave; Stage #2: With copper(ll) bromide In benzene-d6 at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;

potassium cyclopentadienyldicarbonyliron(0) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + FCF=CFFe(CO)2Cp (12152-59-9)

Conditions	Yield
With t-butyl alcohol In tetrahydrofuran byproducts: CF2=CFH, t-BuOCF2CFHBr; under Ar; react. in the presence of t-BuOH; alkenyl halide mixed with FpK soln. pre-cooled at -50 °C; after 10-15 min react. mixt. allowed to reach room temp.; not isolated; NMR;	A 95% B 1%
With PhCH(Et)CN In tetrahydrofuran byproducts: CF2=CFH, CFH=CFC(Et)(Ph)CN, CFHBrCF2C(Et)(Ph)CN; under Ar; react. in the presence of PhCH(Et)CN; alkenyl halide mixed with FpK soln. pre-cooled at -50 °C; after 10-15 min react. mixt. allowed to reach room temp.; not isolated; NMR;	A 77% B 5%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 1,1-dibromo-1,2,2,2-tetrafluoroethane (27336-23-8) → hexafluoro-1,3-butadiene (685-63-2)

Conditions	Yield
Stage #1: 1,1-dibromo-1,2,2,2-tetrafluoroethane With aluminum (III) chloride; zinc In 1-methyl-pyrrolidin-2-one at 70 - 90℃; for 3.2h; Inert atmosphere; Stage #2: 1-bromo-1,2,2-trifluoroethene With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 40℃; for 21.6h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	95%

ethanol (64-17-5) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 1-ethoxy-1,1,2-trifluoro-2-bromoethane (380-78-9)

Conditions	Yield
Stage #1: ethanol With sodium at 20℃; for 0.666667h; Stage #2: 1-bromo-1,2,2-trifluoroethene In ethanol Further stages.;	93%
With potassium hydroxide
With sodium

1-bromo-1,2,2-trifluoroethene (598-73-2) + 2-ethoxycarbonyl-methylisoquinolinium bromide (18010-05-4) → ethyl 1,2-difluoropyrrolo[2,1-a]isoquinolin-3-carboxylate

Conditions	Yield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 24h;	91%

tetrakis(triethylphosphine)palladium (52230-29-2) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → ((C2H5)3P)2PdBr(CFCF2)

Conditions	Yield
In Petroleum ether (N2); bubbling bromotrifluoroethylene through soln. of (Et3P)4Pd (-196°C); stirring for 10 min; warming to room temp.; removal of solvent in vac.; washing (cold n-hexane); chromy. (florisil,methylene chloride); elem. anal.;	90%

decacarbonyldirhenium(0) (14285-68-8) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → rhenium(I) pentacarbonyl bromide (14220-21-4) + cis-[CF2=CF(CO)Re(CO)4Br]Na (1327300-35-5)

Conditions	Yield
With Na#Hg In tetrahydrofuran under Ar; soln. of (Re(CO)5)Na (prepd. from Re2(CO)10 and 0.5% NaHg in THF) mixed with alkenyl halide at room temp.; react. completed in less than 4 min; soln. filtered through Celite; THF removed in vacuo;	A 5% B 90%

1-bromo-1,2,2-trifluoroethene (598-73-2) + trimethyltin(IV)chloride (1066-45-1) → (trifluoro ethylenyl) trimethyl stannane (815-22-5)

Conditions	Yield
With hexaethylphosphorous triamide; benzonitrile In benzonitrile under exclusion of moisture; mixt. of Me3SnCl, hexaethylphosphorus triamide, and benzonitrile was degassed at -196°C; CF2CFBr condensed via vacuum; mixt. warmed to 25°C, stirred for 12 h; distd.;	89%

triethylsilyl chloride (994-30-9) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → triethyl(trifluorovinyl)silane (680-76-2)

Conditions	Yield
With methyllithium In diethyl ether at -78℃; for 4h;	88%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 2-phenacylisoquinolinium bromide (25131-60-6) → (1,2-difluoropyrrolo[2,1-a]isoquinolin-3-yl)phenylmethanone

Conditions	Yield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 24h;	86%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 2-(4-Bromophenoxy)tetrafluoroethanesulfonyl fluoride (252975-60-3) → C10H4F8O3S (823813-09-8)

Conditions	Yield
Stage #1: 1-bromo-1,2,2-trifluoroethene With bromine; zinc; tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide) at 20 - 65℃; for 3.5h; Stage #2: 2-(4-Bromophenoxy)tetrafluoroethanesulfonyl fluoride With tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide) at 75℃; for 10h;	86%

1-bromo-1,2,2-trifluoroethene (598-73-2) + trifluoroethenylzinc bromide (105417-08-1) → hexafluoro-1,3-butadiene (685-63-2)

Conditions	Yield
With diphenylethoxyphosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 20 - 130℃; for 3h; Reagent/catalyst; Temperature;	85.8%
With iron(III) chloride at 5℃; Reagent/catalyst; Temperature; Flow reactor;	80.4%

2-(trifluoromethyl)-3,3-difluorooxaziridine (60247-20-3) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 4-bromo-3-(trifluoromethyl)perfluorooxazolidine (104550-50-7)

Conditions	Yield
at 55 - 100℃; for 18h;	85%

1-bromo-1,2,2-trifluoroethene (598-73-2) + bis(fluoroxy)difluoromethane (16282-67-0) → 4-bromo-2,2,4,5,5-pentafluoro-1,3-dioxolane

Conditions	Yield
In Dichlorodifluoromethane at -70℃; for 4h;	85%

chloro-trimethyl-silane (75-77-4) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 1,1,2-trifluoro-2-trimethylsilylethylene (1427-33-4)

Conditions	Yield
With hexaethylphosphoric triamide In benzonitrile for 20h; Ambient temperature;	85%
Stage #1: 1-bromo-1,2,2-trifluoroethene With chloro-trimethyl-silane; ethylene dibromide; zinc In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Heating; Stage #2: chloro-trimethyl-silane With copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Stage #3: With ethylene glycol In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	74%
With methyllithium In diethyl ether
With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide electrolysis at stainless steel grid cathode and sacrificial zinc anode;
With zinc

1-bromo-1,2,2-trifluoroethene (598-73-2) → C2Br2F3NO4 + Carbonyl fluoride (353-50-4) + carbonyl bromide fluoride (753-56-0) + difluorobromoacetyl fluoride (38126-07-7)

Conditions	Yield
With oxygen; Nitrogen dioxide at 40.25℃; gas-phase; Further byproducts given;	A n/a B n/a C n/a D 85%

1-bromo-1,2,2-trifluoroethene (598-73-2) → 1,1-dibromohexafluorocyclobutane

Conditions	Yield
at 450℃; for 0.00555556h;	85%

C20H15ClFN3OS (952049-71-7) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 5-{5-[4-(2-bromo-1,1,2-trifluoroethoxy)phenyl]-3-methylthiophen-2-yl}-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole (952049-86-4)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 25℃; for 1h;	82%

C21H17ClFN3OS + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 5-{5-[4-(2-bromo-1,1,2-trifluoroethoxy)phenyl]-3,4-dimethylthiophen-2-yl}-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole (952049-89-7)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 25℃; for 1h;	80%

1-bromo-1,2,2-trifluoroethene (598-73-2) + N-benzyl-N'-[(ethoxycarbonyl)methyl]benzimidazolium bromide → ethyl 4-benzyl-2,3-difluoro-4H-pyrrolo[1,2-a]benzimidazole-1-carboxylate

Conditions	Yield
With potassium carbonate; triethylamine In dimethyl sulfoxide at 70℃; for 18h;	79%

cobalticinium fluoride + 1-bromo-1,2,2-trifluoroethene (598-73-2) → C12H10BrCoF4

Conditions	Yield
In tetrahydrofuran at -196 - 20℃; Schlenk technique; Inert atmosphere;	79%

1-bromo-1,2,2-trifluoroethene (598-73-2) + perfluoro-NN'-dimethylethane-1,2-bis(amino-oxyl) diradical (36525-64-1) → 7-bromo-3,3,4,4,7,8,8-heptafluoro-2,5-bis(trifluoromethyl)-1,6-dioxa-2,5-diazacyclo-octane

Conditions	Yield
under 19 Torr; for 48h; Ambient temperature;	78%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 4-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide (7250-28-4) → (1,2-difluoro-7-methylindolizin-3-yl)phenylmethanone

Conditions	Yield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 24h;	77%

1-bromo-1,2,2-trifluoroethene (598-73-2) + benzoyl chloride (98-88-4) + hexafluoro-2-butyne (692-50-2) → 2,2,3-trifluoro-4,5-bis(trifluoromethyl)-6-phenyl-2H-pyran (1206484-46-9)

Conditions	Yield
Stage #1: 1-bromo-1,2,2-trifluoroethene With zinc In N,N-dimethyl-formamide Inert atmosphere; Stage #2: With copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #3: benzoyl chloride; hexafluoro-2-butyne stereospecific reaction; Further stages;	76%

1-bromo-1,2,2-trifluoroethene (598-73-2) + N-(ethoxycarbonylmethyl)pyridinium bromide (17282-40-5) → ethyl 1,2-difluoroindolizine-3-carboxylate

Conditions	Yield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 24h;	75%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 2-phenacyl-isoquinolinium; chloride (73825-51-1) → (1,2-difluoropyrrolo[2,1-a]isoquinolin-3-yl)phenylmethanone

Conditions	Yield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 24h;	74%

C21H17ClFN3OS (952049-85-3) + 1-bromo-1,2,2-trifluoroethene (598-73-2) → 5-{4-[4-(2-bromo-1,1,2-trifluoroethoxy)phenyl]-3,5-dimethylthiophen-2-yl}-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole (952049-96-6)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 25℃; for 1h;	74%

1-bromo-1,2,2-trifluoroethene (598-73-2) + 1-benzyl-3-(2-oxo-2-phenylethyl)benzimidazolium bromide → (4-benzyl-2,3-difluoro-4H-pyrrolo[1,2-a]benzimidazol-1-yl)phenylmethanone

Conditions	Yield
With potassium carbonate; triethylamine In dimethyl sulfoxide at 70℃; for 18h;	72%

1-bromo-1,2,2-trifluoroethene (598-73-2) + copper(I) bromide (7787-70-4) + zinc (7440-66-6) → trifluorovinyl copper (102682-87-1)

Conditions	Yield
In N,N-dimethyl-formamide byproducts: ZnBr2; N2; slight excess of Zn powder added to alkene soln.; mild exothermic reaction after induction period; removal of excess Zn by press. filtrn. under N2; stirring mixt. at 0 °C for half h with CuBr; final warming to room temp.; (19)F NMR;	72%

1-bromo-1,2,2-trifluoroethene (598-73-2) + hexafluoro-2-butyne (692-50-2) → C6HF9 (1206484-52-7)

Conditions	Yield
Stage #1: 1-bromo-1,2,2-trifluoroethene With zinc In N,N-dimethyl-formamide Inert atmosphere; Stage #2: With copper(I) bromide In N,N-dimethyl-formamide Inert atmosphere; Stage #3: hexafluoro-2-butyne stereospecific reaction; Further stages;	72%

1-bromo-1,2,2-trifluoroethene (598-73-2) + Diphenylacetonitrile (86-29-3) → 4-bromo-3,3,4-trifluoro-2,2-diphenyl-butyronitrile + (Z)-4-Bromo-3,4-difluoro-2,2-diphenyl-but-3-enenitrile

Conditions	Yield
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran Stage #2: 1-bromo-1,2,2-trifluoroethene In tetrahydrofuran at 20℃; for 0.5h;	A 15 % Spectr. B 70%

Upstream product

• 354-04-1 1,2-dibromo-1,1,2-trifluoroethane 
• 421-06-7 2-bromo-1,1,1-trifluoroethane 
• 56184-59-9 (pentafluoro ethyl) magnesiumbromide 
• 116-14-3 polytetrafluoroethylene 
• 1375484-85-7 N(C₄H₉)4⁽¹⁺⁾*CF₂CFBF₃^(1-)=N(C₄H₉)4[CF₂CFBF₃] 
• 22687-88-3 (1,2-dibromotrifluoroethyl)pentafluorosulfur(VI) 
• 75-82-1 1,2-dibromo-1,1-difluoroethane 
• 117113-33-4 3-bromo-3-(trifluoromethyl)diazirine 

Downstream Products

• 380-78-9 1-ethoxy-1,1,2-trifluoro-2-bromoethane 
• 679-95-8 3-bromo-2,2,3-trifluoro-propionic acid 
• 354-20-1 1-Chlor-2-brom-1,1,2-trifluorethan 
• 359-11-5 1,1,2-trifluoroethylene 
• 679-90-3 bromo-2-trifluoro-1,1,2-ethyl-methyl ether 
• 69249-06-5 (perfluorovinyl)diphenylphosphine 
• 1730-24-1 1,2-Difluor-1-brom-1,4-pentadien 
• 708-84-9 α-Fluor-β-phenyl-crotonsaeure 
• 15052-92-3 2-(trifluoro methyl) 2-hydroxy (perfluoro buten-⁽³⁾) 
• 37021-41-3 Methyl-1,1,2-trifluor-2,2-dibromethyl-ether 
• 127357-38-4 N-(benzyloxycarbonyl)-α-hydroxy-glycine methyl ester 
• 106872-28-0 3,4,4-trifluoro-2-benzyloxycarbonylamino-but-3-enoic acid methyl ester 
• 699-39-8 perfluoro-1,3-cyclopentadiene 
• 124-72-1 1,1,1,2-tetrafluorobromoethane 

Relevant articles and documents

Direct Transformation of Tetrafluoroethylene to Trifluorovinylzinc via sp2C-F Bond Activation

Trifluorovinylzinc is a common synthetic intermediate for trifluorovinyl derivatives, including α,β,β-trifluorostyrenes and hexafluorobutadiene. Here, we report a novel synthetic approach for the formation of trifluorovinylzinc chloride via a C-F bond activation of tetrafluoroethylene (TFE), which is an industrially cost-effective bulk feedstock with a negligible GWP. The present system provides a practical synthetic route to various trifluorovinyl derivatives with very low energy consumption.

Reactions of perfluorinated alkenyl-, alkynyl-, alkyltrifluoroborates, and selected hydrocarbon analogues with the halogenating agents Hal2 (Hal = F, Cl, Br), "brF" (BrF3-Br2 1:1), and ICl

Reactions of [Bu4N][RBF3] [R = CnF 2n+1CF=CF (cis, trans), CF2=CF, CF2=C(CF 3), trans-C4H9CF=CF, trans-C6H 5CF=CF, C4H9CH=CH (cis, trans), CF 3C≡C, and C4H9C≡C] with chlorine, bromine, BrF3 + Br2 (as equivalent of "BrF"), and ICl in solution (CH2Cl2, CHCl3, CF 3CH2CF2CH3) led to 1, 2-addition of halogen and/or replacement of boron by halogen (halodeboration). The reaction of [Bu4N][CF3C≡CBF3] with less than equimolar amounts of diluted fluorine (5 %) in 1, 1, 1, 3, 3-pentafluorobutane (PFB) showed only [Bu4N][CF3CF2CF 2BF3] as fluorine addition product besides extensive fluorodeboration. Suspensions of the insoluble K[CF2=CFBF 3] salt reacted with Cl2 and Br2 in CH 2Cl2 giving preferentially products of halogen addition across the C=C bond. In reactions with ICl iododeboration with formation of CF2=CFI occurred besides 1, 2-addition with formation of [CF 2I-CFClBF3]-. The halodeboration reaction of[Bu4N][trans-C4H9CF=CFBF3] with Br2, "BrF", and ICl, of K[trans-C6H 5CF=CFBF3] with Br2, and of [Bu 4N][trans-C4F9CF=CFBF3] with ICl proceeded stereospecifically. Copyright