Bromobenzene

Bromobenzene

Bromobenzene

Chemical compound

Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C6H5Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.

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Synthesis and reactions

Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as aluminium chloride or ferric bromide.[3]

Bromobenzene is used to introduce a phenyl group into other compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid.[4] Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine.

Toxicity

Animal tests indicate low toxicity.[5] Little is known about chronic effects.[6][7]

For liver toxicity, the 3,4-epoxide is a proposed intermediate.[8]

References

  1. [1]
    Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 10, 31. doi:10.1039/9781849733069-00001. ISBN 978-0-85404-182-4.
  2. [2]
    Nayak, Jyoti N.; Aralaguppi, Mrityunjaya I.; Aminabhavi, Tejraj M. (2003). "Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Ethyl Chloroacetate + Cyclohexanone, + Chlorobenzene, + Bromobenzene, or + Benzyl Alcohol at (298.15, 303.15, and 308.15) K". Journal of Chemical & Engineering Data. 48 (3): 628–631. doi:10.1021/je0201828. ISSN 0021-9568.
  3. [3]
    "Preparation of bromobenzene and iodobenzene". Journal of the Chemical Society, Abstracts. 38: 316. 1880. doi:10.1039/CA8803800307.
  4. [4]
    G. S. Hiers (1927). "Triphenylstibine". Org. Synth. 7: 80. doi:10.15227/orgsyn.007.0080.
  5. [5]
    e.V., Deutsche Gesetzliche Unfallversicherung. "IFA - Databases on hazardous substance (GESTIS): GESTIS database on hazardous substances". www.dguv.de. Retrieved 2018-03-29.
  6. [6]
    Szymańska, J. A.; Piotrowski, J. K. (November 2000). "Hepatotoxicity of monobromobenzene and hexabromobenzene: effects of repeated dosage in rats". Chemosphere. 41 (10): 1689–1696. Bibcode:2000Chmsp..41.1689S. doi:10.1016/s0045-6535(00)00064-3. ISSN 0045-6535. PMID 11057697.
  7. [7]
    National Research Council (1977). Drinking Water and Health: Volume 1. pp. 693. doi:10.17226/1780. ISBN 9780309026192. PMID 25121315.
  8. [8]
    "TOXICOLOGICAL REVIEW OF BROMOBENZENE" (PDF). Integrated Risk Information System. U.S. Environmental Protection Agency.
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