|Preferred IUPAC name
Acetyl methyl bromide
Bromomethyl methyl ketone
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||136.976 g·mol−1|
|Melting point||−36.5 °C (−33.7 °F; 236.7 K)|
|Boiling point||137 °C (279 °F; 410 K)|
|Vapor pressure||1.1 kPa (20 °C)|
|Flash point||51.1 °C (124.0 °F; 324.2 K)|
|Safety data sheet (SDS)||MSDS at ILO|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Bromoacetone is prepared by combining bromine and acetone, with catalytic acid. 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. If a base is present, bromoform is obtained instead, by the haloform reaction.
It was used in World War I as a chemical weapon, called BA by British and B-Stoff (Weisskreuz) by Germans. Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone by reaction with aqueous sodium hydroxide.