Chemistry:Tribromochloromethane
Tribromochloromethane is a tetrahalomethane with the chemical formula CBr
3Cl. This is an organic compound containing three bromine atoms and one chlorine atom attached to the methane backbone.[1][2]
Synthesis
Tribromochloromethane can be prepared by the reflux reaction of carbon tetrachloride and aluminum tribromide[3] or by the reaction of chlorocyclohexane and carbon tetrabromide in presence of ferric bromide.[4]
- CCl
4 + AlBr
3 ⟶ CBr
3Cl + AlCl
3 - CBr
4 + C
6H
11Cl ⟶ CBr
3Cl + C
6H
11Br
- CCl
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.[5]
Chemical properties
Tribromochloromethane reacts with concentrated sulfuric acid to produce carbonyl bromide chloride:[6]
- CBr
3Cl + H
2SO
4 → COBrCl + 2HBr + SO
3
- CBr
References
- ↑ "Tribromochloromethane". NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C594150.
- ↑ Armarego, W. L. F.; Chai, Christina Li Lin (2013) (in en). Purification of Laboratory Chemicals. Butterworth-Heinemann. p. 210. ISBN 978-0-12-382161-4. https://books.google.com/books?id=XWYqh1an5sQC&dq=Tribromochloromethane&pg=PA210. Retrieved 10 September 2025.
- ↑ Tanaka, Ryuichi; Zhèng, Shì-Qín; Kawaguchi, Kenji; Tanaka, Takehide (1 January 1980). "Nucleophilic attack on halogeno(phenyl)acetylenes by halide ions" (in en). Journal of the Chemical Society, Perkin Transactions 2 (11): 1714–1720. doi:10.1039/P29800001714. ISSN 1364-5471. https://pubs.rsc.org/en/content/articlelanding/1980/p2/p29800001714. Retrieved 10 September 2025.
- ↑ 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. https://pubs.acs.org/doi/abs/10.1021/jo00274a013. Retrieved 10 September 2025.
- ↑ Katritzky, Alan R.; Gilchrist, Thomas L.; Meth-Cohn, Otto; Rees, Charles Wayne (21 March 2003) (in en). Comprehensive Organic Functional Group Transformations. Elsevier. p. 222. ISBN 978-0-08-042704-1. https://books.google.com/books?id=YzBveZGm0GEC&dq=Tribromochloromethane&pg=PA222. Retrieved 10 September 2025.
- ↑ Ryan, T. A.; Seddon, E. A.; Seddon, K. R.; Ryan, C. (24 May 1996) (in en). Phosgene: And Related Carbonyl Halides. Elsevier. p. 880. ISBN 978-0-08-053880-8. https://books.google.com/books?id=fM43Ny2eFS8C&dq=Tribromochloromethane&pg=PA880. Retrieved 10 September 2025.
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