Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.
Propargyl bromide can also be used as an intermediate for the synthesis of organic compounds, including agrochemicals and pharmaceuticals. In the 1960s, it was used in a soil fumigant called Trizone.[1]
Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[2]
Propargyl bromide is an alkylating agent. With dimethylsulfide, it reacts to give the sulfonium salt:[3]
It also alkylates even weakly basic amines such as aniline.[4]
Aldehydes react with propargyl bromide in a Barbier-type reaction to yield alkynyl alcohols:[5]
At low temperatures, upon treatment with magnesium, propargyl bromide gives the Grignard reagent formally derived from allenyl bromide, i.e., CH2=C=CHMgBr.