Propargyl bromide
Propargyl bromide, also known as 3-bromo-1-propyne, is an organic compound with the chemical formula CHCCH2Br. It is a halogenated organic compound consisting of an alkyl functional group with 2-propynyl group linked to bromide. It has a lachrymatory effect, like related compounds. The compound is a useful reagent in organic synthesis.
Applications
In the 1960s, propargyl bromide was first used in a soil fumigant called Trizone.
Propargyl bromide can also be used as an intermediate for the synthesis of organic compounds, including agrochemicals and pharmaceuticals. It forms a Grignard reagent at low temperatures, for example.
Production
Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide:
Reactions
Propargyl bromide can be used in enyne metathesis of propargylic amines, propargylation of spiro ketones, production of allylic alcohols, and enone complexes.
Aldehydes may be reacted with propargyl bromide in a Barbier-type reaction to yield alkyne alcohols as well:
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