Bromotrifluoroethylene (BTFE) is a halogenated

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

derivative with the chemical formula . It is a highly flammable colourless gas with a musty odour resembling

phosgene Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...

. It can polymerise spontaneously.Arthur J. Elliott
''Bromotrifluoroethylene''
in Kirk-Othmer Encyclopedia of Chemical Technology

Preparation

Bromotrifluoroethylene can be prepared from

chlorotrifluoroethylene Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethy ...

with high yields: : : It was first prepared by the Belgian chemist

Frédéric Swarts Frédéric Jean Edmond Swarts (2 September 1866 – 6 September 1940) was a Belgian chemist who prepared the first chlorofluorocarbon, CF2Cl2 (Freon-12) as well as several other related compounds. He was a professor in the civil engineering at t ...

in 1899.''Industrial Polymers and Radiation: Proceedings of the Symposium Held at Sardar Patel University'', Vallabh Vidyanagar, Gujarat, February 12–14, 1979.

Reactions and uses

Bromotrifluoroethylene forms metal complexes with substituted

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

compounds and

platinum Platinum is a chemical element; it has Symbol (chemistry), symbol Pt and atomic number 78. It is a density, dense, malleable, ductility, ductile, highly unreactive, precious metal, precious, silverish-white transition metal. Its name origina ...

(II).V.A. Mukhedkar, B.J. Kavathekar, A.J. Mukhedkar
''Reactions of metal complexes Rearrangement reactions of bromotrifluoroethylene-bis(substituted phosphine)-platinum (II)''
Journal of Inorganic and Nuclear Chemistry, Volume 37, Issue 2, February 1975, Pages 483-485 BTFE can polymerise on standing. Spontaneous polymerisation may be inhibited by addition of

tributylamine Tributylamine (TBA) is an organic compound with the molecular formula (C4H9)3N. It is a colorless liquid with an amine-like odor. Uses Tributylamine is used as a catalyst (proton acceptor) and as a solvent in organic syntheses and polymerization ...

.''Fluorine chemistry: a comprehensive treatment'' (1995)
pages 479–480
/ref> UV light and heat may accelerate polymerisation. It participates in various co-polymerisation reactions. BTFE telomers are oily liquids sold under the tradename BFC oil. The telomers can be prepared with fluorotrichloromethane or

tetrachloromethane Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...

as telogens. If tetrachloromethane is used for the telomerisation, it will have -CCl terminals. It is a useful reagent for the synthesis of trifluorovinyl compounds.

References

{{Reflist Bromoalkenes Fluoroalkenes Organofluorides