Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.

Preparation

Hydrohalogenation

Allyl bromide is produced commercially from allyl alcohol and hydrobromic acid: 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 nucleophiles, such as amines, carbanions, alkoxides, etc., to introduce the allyl group: 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 metal in dry ether to form allylmagnesium bromide, a Grignard reagent: