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Propargyl bromide
Chemical compound From Wikipedia, the free encyclopedia
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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.
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Applications and production
Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[2]
Reactions
Propargyl bromide is an alkylating agent. For example, it reacts with dimethylsulfide, it reacts to give the sulfonium salt:[3]
- HCCCH2Br + S(CH3)2 → [HCCCH2S(CH3)2]Br
It 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.[6]
Propargyl bromide and its ether derivatives participate in azide-based click reactions.[7]
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Safety
Propargyl bromide is a lachrymator and an alkylating agent,[8] This liquid acetylenic endothermic compound may be decomposed by mild shock, and when heated under confinement, it decomposes with explosive violence and may detonate. Addition of 20—30 wt% of toluene makes propargyl bromide insensitive in laboratory impact and confinement tests.[9]
See also
References
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