Bromotrichloromethane

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Bromotrichloromethane
Names
Preferred IUPAC name
bromo(trichloro)methane
Other names
carbon bromotrichloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.806 Edit this at Wikidata
EC Number
  • 200-886-0
UNII
  • InChI=1S/CBrCl3/c2-1(3,4)5
    Key: XNNQFQFUQLJSQT-UHFFFAOYSA-N
  • C(Cl)(Cl)(Cl)Br
Properties
CBrCl3
Molar mass 198.27 g·mol−1
Appearance liquid
Density 2.401 g/cm³
Melting point −6 °C (21 °F; 267 K)
Boiling point 105 °C (221 °F; 378 K)
practically insoluble
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
Flash point 32.6 °C
Related compounds
Related compounds
 Bromodichloromethane; Tribromochloromethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bromotrichloromethane is a tetrahalomethane with the chemical formula CBrCl3. This is a halomethane containing one bromine atom and three chlorine atoms attached to the methane backbone.[2]

Synthesis

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Bromotrichloromethane can be obtained by reacting carbon tetrachloride with hydrogen bromide or aluminum bromide.[3] It can also be obtained by reacting trichloromethane with bromine at 225 °C to 400 °C or potassium trichloroacetate with bromine at 120 °C.[4]

Cl3CCO2K + Br2 → CBrCl3 + CO2 + KBr

Physical properties

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Bromotrichloromethane is a volatile, non-flammable, colorless liquid with a pungent odor that is practically insoluble in water but highly miscible with organic solvents. It is readily evaporated upon exposure to the air. The compound is toxic.[5]

Uses

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Bromotrichloromethane is used as a chain transfer agent for the radical polymerization of methacrylates and as a brominating agent.[6]

References

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  1. ^ "Bromotrichloromethane". Sigma Aldrich. Retrieved 5 September 2025.
  2. ^ Crich, David (30 May 2013). Reagents for Radical and Radical Ion Chemistry. John Wiley & Sons. p. 12. ISBN 978-1-118-63489-9. Retrieved 5 September 2025.
  3. ^ Skell, P. S; Baxter, H. N; Tanko, J. M (1 January 1986). "Reactions of BrCl with alkyl radicals". Tetrahedron Letters. 27 (43): 5181–5184. doi:10.1016/S0040-4039(00)85163-1. ISSN 0040-4039. Retrieved 5 September 2025.
  4. ^ Gilchrist, Thomas L. (1995). Comprehensive Organic Functional Group Transformations (1 ed.). Oxford: Elsevier. p. 221. ISBN 0-08-042704-9. Retrieved 5 September 2025.
  5. ^ Anderson, Bruce; Peyster, Ann de; Gad, Shayne C.; Hakkinen, P. J. Bert; Kamrin, Michael; Locey, Betty; Mehendale, Harihara M.; Pope, Carey; Shugart, Lee (31 May 2005). Encyclopedia of Toxicology. Elsevier. ISBN 978-0-08-054800-5. Retrieved 5 September 2025.
  6. ^ "Bromtrichlormethan". gestis.dguv.de. Retrieved 5 September 2025.