Tribromochloromethane

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Tribromochloromethane
Names
Preferred IUPAC name
Tribromo(chloro)methane
Other names
  • Bromoform-chlorine
  • Chlorotribromomethane[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.936 Edit this at Wikidata
EC Number
  • 209-827-3
UNII
  • InChI=1S/CBr3Cl/c2-1(3,4)5
    Key: GKXZMEXQUWZGJK-UHFFFAOYSA-N
  • C(Cl)(Br)(Br)Br
Properties
CBr3Cl
Molar mass 287.17 g·mol−1
Appearance solid[2]
Density 3.0 g/cm3
Melting point 54 °C (129 °F; 327 K)
Boiling point 156.1 °C (313.0 °F; 429.2 K)
soluble
Hazards
Flash point 52.8±8.5 °C
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tribromochloromethane is a tetrahalomethane with the chemical formula CBr3Cl. This is an organic compound containing three bromine atoms and one chlorine atom attached to the methane backbone.[3][4]

Synthesis

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Tribromochloromethane can be prepared by the reflux reaction of carbon tetrachloride and aluminum tribromide[5] or by the reaction of chlorocyclohexane and carbon tetrabromide in presence of ferric bromide.[6]

CCl4 + AlBr3 ⟶ CBr3Cl + AlCl3
CBr4 + C6H11Cl ⟶ CBr3Cl + C6H11Br

Also, dibromoformaldehyde oxime reacts with aqueous mercury dichloride solution, and then reacts with bromine and sodium acetate to obtain dibromochloronitrosomethane, which can then be refluxed with bromine to obtain tribromochloromethane.[7]

Chemical properties

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Tribromochloromethane reacts with concentrated sulfuric acid to produce carbonyl bromide chloride:[8]

CBr3Cl + H2SO4 → COBrCl + 2HBr + SO3

References

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  1. ^ "NCATS Inxight Drugs — TRIBROMOCHLOROMETHANE". drugs.ncats.io. Retrieved 10 September 2025.
  2. ^ Journal of Research of the National Bureau of Standards. U.S. Government Printing Office. 1950. p. 504. Retrieved 10 September 2025.
  3. ^ "Tribromochloromethane". NIST. Retrieved 10 September 2025.
  4. ^ Armarego, W. L. F.; Chai, Christina Li Lin (2013). Purification of Laboratory Chemicals. Butterworth-Heinemann. p. 210. ISBN 978-0-12-382161-4. Retrieved 10 September 2025.
  5. ^ Tanaka, Ryuichi; Zhèng, Shì-Qín; Kawaguchi, Kenji; Tanaka, Takehide (1 January 1980). "Nucleophilic attack on halogeno(phenyl)acetylenes by halide ions". Journal of the Chemical Society, Perkin Transactions 2 (11): 1714–1720. doi:10.1039/P29800001714. ISSN 1364-5471. Retrieved 10 September 2025.
  6. ^ Yoon, K. B.; Kochi, J. K. (1 June 1989). "Catalytic bromide and iodide exchange of alkyl chlorides with hydrogen bromide and hydrogen iodide". The Journal of Organic Chemistry. 54 (13): 3028–3036. doi:10.1021/jo00274a013. ISSN 0022-3263. Retrieved 10 September 2025.
  7. ^ Katritzky, Alan R.; Gilchrist, Thomas L.; Meth-Cohn, Otto; Rees, Charles Wayne (21 March 2003). Comprehensive Organic Functional Group Transformations. Elsevier. p. 222. ISBN 978-0-08-042704-1. Retrieved 10 September 2025.
  8. ^ Ryan, T. A.; Seddon, E. A.; Seddon, K. R.; Ryan, C. (24 May 1996). Phosgene: And Related Carbonyl Halides. Elsevier. p. 880. ISBN 978-0-08-053880-8. Retrieved 10 September 2025.