Tribromofluoromethane
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| Names | |
|---|---|
| Preferred IUPAC name
Tribromo(fluoro)methane | |
| Other names
Tribromofluoromethane
Tribromo-fluoro-methane Fluorotribromomethane Halon 1103 FC-11B3 R 11B3 | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.005.942 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| CBr3F | |
| Molar mass | 270.72 g/mol |
| Appearance | Clear yellow liquid |
| Density |
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| Melting point | −73 °C (−99 °F; 200 K) |
| Boiling point | 108 °C (226 °F; 381 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tribromofluoromethane[1] also known as Halon 1103 or R 11B3, is a fully halogenated mixed halomethane or, more exactly, a bromofluorocarbon (BFC). It is a colorless to yellow liquid[2]
Tribromofluoromethane can be used in fire extinguishers.
Table of physical properties
[edit]| Property | Value |
|---|---|
| Refractive index, n, at 20 °C | 1.5216 |
| Surface tension at 20 °C | 31.68 mN·m−1 |
| Viscosity at 0 °C | 2.09 mPa·s, 2.09 cP |
History
[edit]Tribromofluoromethane was first synthesised in 1919 by Hans Rathburg.[3] It was later prepared by reacting carbon tetrabromide with antimony trifluoride and elemental bromine[4] by heating at 120 to 130 °C (248 to 266 °F; 393 to 403 K) for 1 hour and having the tribromofluormethane distill off.[5]
Chemistry
[edit]Pyrolysis of tribromofluoromethane yields hexafluorobenzene at up to a 45 percent yield,[6] plus bromine, alongside small quantities of bromopentafluorobenzene.[7]
The bromines in tribromofluoromethane can be substituted by reactive metals like lithium and zinc using organometallic compounds, ultimately creating fluorinated alcohols by addition of carbonyl compounds.[8]
Tribromofluoromethane also forms phosphorus ylides which can be used to synthesise bromofluoro-substituted terminal alkenes.[9] Similar loss of bromine takes place through cyclisation with hydrazones to form 4-fluoro pyrazoles.[10]
References
[edit]- ^ PubChem. "Tribromofluoromethane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-25.
- ^ "Tribromofluoromethane 98.0 %, TCI America, Quantity: 5g | Fisher Scientific". www.fishersci.com. Retrieved 2022-11-25.
- ^ Finch, Charles Richard (1955). A Study of Methods for the Production of Bromotrifluoromethane and Dibromodifluoromethane (Graduate thesis). University of Maryland.
- ^ Birchall, J. M.; Haszeldine, R. N. (1959). "Polyfluoroarenes. Part I. Pentafluorophenol". Journal of the Chemical Society: 13–17.
- ^ Armarego, W.L.F. (March 14, 2017). Purification of Laboratory Chemicals. Elsevier Science. p. 217. ISBN 9780128054567.
- ^ Hellmann, Margaret; Peters, Ernest; Pummer, Walter J.; Wall, Leo A. (April 10, 1957). "Hexafluorobenzene from the Pyrolysis of Tribromofluoromethane". Journal of the American Chemical Society. 79 (21): 5654–5656.
- ^ Wall, Leo A.; Fearn, James E.; Pummer, Walter J; Lowry, Robert E (June 1961). "Preparation of Fluoro- and Bromofluoroaryl Compounds by Copyrolysis of Bromofluoroalkanes". Journal of Research of the National Bureau of Standards for Physical Chemistry. 65A (3): 239–242.
- ^ Hata Takeshi (23 March 2000). Title Studies on the Synthetic Aspects of Fluoromethylmetal Reagents Derived from Tribromofluoromethane (Thesis). Kyoto University. p. 4.
- ^ Barlow, M.G.; Taylor, D.R. (1974). "Per- and Poly-fluorinated Olefins, Dienes, Heterocumulenes and Acetylenes". In Banks, R.E.; Barlow, M.G. (eds.). Fluorocarbon and Related Chemistry: Volume 2. p. 47.
- ^ Prieto, Alexis; Bouyssi, Didier; Monteiro, Nuno (2017). "Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CBr3F: Access to 4-Fluoropyrazoles". Journal of Organic Chemistry. 82 (6): 3311–3316.
External links
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