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Bromoacetone is a chemical compound with the formula CH3COCH2Br. This colorless liquid is a lachrymatory agent. It is a precursor to other organic compounds.
Bromoacetone was first prepared in the 19th century. It was used in World War I as a chemical weapon, called BA by British and B-stoff (white cross) by Germans. Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.
Bromoacetone is naturally present (less than 1%) in the essential oil of a seaweed from the vicinity of the Hawaiian Islands. In atmosphere it is degraded by the photochemically produced hydroxyl radicals.
Bromoacetone is available commercially, sometimes stabilized with magnesium oxide.
As with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products.
Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone (b.p. 35–47°/12 mm, CAS #116-09-6).
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bromoacetone". A list of authors is available in Wikipedia.|