Bromotrifluoroethylene

Bromotrifluoroethylene

Names
IUPAC name bromotrifluoroethene
Other names trifluorovinyl bromide, trifluorobromoethylene
Identifiers
CAS Number	598-73-2
3D model (JSmol)	Interactive image
ChemSpider	11237
ECHA InfoCard	100.009.045
EC Number	209-948-1
PubChem CID	11730
UN number	2419
CompTox Dashboard (EPA)	DTXSID0060513
InChI InChI=1S/C2BrF3/c3-1(4)2(5)6 Key: AYCANDRGVPTASA-UHFFFAOYSA-N
SMILES C(=C(F)Br)(F)F
Properties
Chemical formula	C2BrF3
Molar mass	160.921 g·mol^−1
Appearance	colourless gas
Odor	moldy,[1] phosgene-like[2]
Boiling point	–2.5°C[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	spontaneous polymerisation, flammable[3]
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H220, H280, H315, H319, H330, H332, H335
Precautionary statements	P203, P210, P222, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P320, P321, P332+P317, P337+P317, P362+P364, P377, P381, P403, P403+P233, P405, P410+P403, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bromotrifluoroethylene (BTFE) is a halogenated ethylene derivative with the chemical formula F₂CCBrF. It is a highly flammable colourless gas with a musty odour resembling phosgene. It can polymerise spontaneously.[3]

Preparation

Bromotrifluoroethylene can be prepared from chlorotrifluoroethylene with high yields:[3][4]

F₂C=ClF + HBr → CF₂BrCHClF + Zn → CF₂=CHF + ZnBrCl

CF₂=CHF + Br₂ → CF₂BrCHBrF + KOH → CF₂CHBr + KBr + H₂O

It was first prepared by the Belgian chemist Frédéric Swarts in 1899.[5]

Reactions and uses

Bromotrifluoroethylene forms metal complexes with substituted phosphine compounds and platinum(II).[6]

BTFE can polymerise on standing. Spontaneous polymerisation may be inhibited by addition of tributylamine.[4] UV light and heat may accelerate polymerisation.[4] It participates in various co-polymerisation reactions.[2] BTFE telomers are oily liquids sold under the tradename BFC oil. The telomers can be prepared with fluorotrichloromethane or tetrachloromethane as telogens. If tetrachloromethane is used for the telomerisation, it will have -CCl₃ terminals.[5] It is a useful reagent for the synthesis of trifluorovinyl compounds.[3]

References

1. Hazardous Substance Fact Sheet, New Jersey Department of Health PDF
2. Yaws, C. L., Braker, W. (2001). Matheson gas data book. Page 69
3. Arthur J. Elliott, Bromotrifluoroethylene in Kirk-Othmer Encyclopedia of Chemical Technology
4. Fluorine chemistry: a comprehensive treatment (1995), pages 479–480
5. Industrial Polymers and Radiation: Proceedings of the Symposium Held at Sardar Patel University, Vallabh Vidyanagar, Gujarat, February 12–14, 1979.
6. 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