Allyl bromide ( 3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes
Preparation
Hydrohalogenation
Allyl bromide is produced commercially from
allyl alcohol and
hydrobromic acid:
- CH2=CHCH2OH + HBr → CH2=CHCH2Br + H2O
It can also be prepared by the halogen-exchange reaction between
allyl chloride and hydrobromic acid or by the allylic bromination of
propene.
Reactions and uses
Allyl bromide is an electrophilic alkylating agent.
It reacts with
Nucleophile, such as
Amine,
Carbanion,
Alkoxide, etc., to introduce the
allyl group:
- CH2=CHCH2Br + Nu− → CH2=CHCH2Nu + Br− (Nu− is a nucleophile)
It is used in the synthesis of compounds containing the allyl functionality, such as the pharmaceuticals
methohexital,
secobarbital and
thiamylal.
Allyl bromide reacts with Magnesium in dry Diethyl ether to form allylmagnesium bromide, a Grignard reagent:
- CH2=CHCH2Br + Mg → CH2=CHCH2MgBr
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