Tribromofluoromethane
Chemical compound
From Wikipedia, the free encyclopedia
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]
| |
| Names | |
|---|---|
| Preferred IUPAC name
Tribromo(fluoro)methane | |
| Other names
Tribromofluoromethane Tribromo-fluoro-methane Fluorotribromomethane Halon 1103 FC-11B3 R 11B3 | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.005.942 |
| EC Number |
|
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| CBr3F | |
| Molar mass | 270.72 g/mol |
| Appearance | Clear yellow liquid |
| Density |
|
| 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 |
Irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Tribromofluoromethane can be used in fire extinguishers.
Table of physical properties
| 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
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
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]
