Inorganic chemistry, avinyl halide is a compound with the formula CH₂=CHX (X =halide). The termvinyl is often used to describe any alkenyl group. For this reason, alkenyl halides with the formula RCH=CHX are sometimes called vinyl halides. From the perspective of applications, the dominant member of this class of compounds isvinyl chloride, which is produced on the scale of millions of tons per year as a precursor topolyvinyl chloride.^[1]Polyvinyl fluoride is another commercial product. Related compounds includevinylidene chloride andvinylidene fluoride.

Vinyl chloride is produced by dehydrochlorination of 1,2-dichloroethane.^[1]

Due to their high utility, many approaches to vinyl halides have been developed, such as:

• reactions of vinylorganometallic species with halogens

• Takai olefination

• Stork-Zhao olefination with, e.g.,(Chloromethylene)triphenylphosphorane - a modification of theWittig reaction

• Olefin metathesis^[2][3]

Vinyl bromide and related alkenyl halides form theGrignard reagent and relatedorganolithium reagents. Alkenyl halides undergo base elimination to give the correspondingalkyne. Most important is their use incross-coupling reactions (e.g.Suzuki-Miyaura coupling,Stille coupling,Heck coupling, etc.).

• Vinyl iodide functional group

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