Bromobenzene is an
aryl halide, C
6H
5Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
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.
Bromobenzene is used to introduce a
phenyl group into other compounds. One method involves its conversion to the
Grignard reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...
,
phenylmagnesium bromide
Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is o ...
. This reagent can be used, e.g. in the reaction with
carbon dioxide to prepare
benzoic acid. 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. Little is known about chronic effects.
For liver toxicity, the 3,4-epoxide are proposed intermediates.
See also
*
Fluorobenzene
Fluorobenzene is the chemical compound with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds.
Preparation
PhF was first reported in 1886 by O. Wallach at the University of Bonn, who ...
*
Chlorobenzene
*
Iodobenzene
References
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Bromoarenes
Phenyl compounds