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IUPAC name 1-Bromoacetone
Other names Bromoacetone
Acetonyl bromide
Acetyl methyl bromide
Bromomethyl methyl ketone
UN 1569
CAS number 598-31-2
PubChem 11715
RTECS number UC0525000
InChI InChI=1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
Molecular formula C3H5BrO
Molar mass 136.99 g/mol
Appearance Colorless lachrymator
Density 1.634 g/cm³
Melting point

-36.5 °C

Boiling point

137 °C

Vapor pressure 1.1 kPa (20 °C)
Flash point 51.1 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.[1] 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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.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.[2] In atmosphere it is degraded by the photochemically produced hydroxyl radicals.


Bromoacetone is available commercially, sometimes stabilized with magnesium oxide.

Bromoacetone is prepared by reacting bromine and acetone,[3] with catalytic acid or base.

CH3C(O)CH3 + Br2 → CH3C(O)CH2Br + HBr

As with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine.[4] 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).[5]

See also

  • Use of poison gas in World War I


  1. ^ Sokolowsky, Berichte volume 9, pp. 1687 (1876).
  2. ^ B. Jay Burreson, Richard E. Moore, and Peter P. Roller (1976). "Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta)". Journal of Agricultural and Food Chemistry 24 (4): 856 - 861. doi:10.1021/jf60206a040.
  3. ^ Levene, P. A. (1943). "Bromoacetone". Org. Synth.; Coll. Vol. 2: 88. 
  4. ^ William Reusch. Carbonyl Reactivity. VirtualText of Organic Chemistry. Retrieved on 2007-10-27.
  5. ^ Levene, P. A.; Walti, A. (1943). "Acetol". Org. Synth.; Coll. Vol. 2: 5. 
  • Merck Index, 11th Edition, 1389
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.
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