Bromacetone

Bromoacetone[1]
Identifiers
CAS number 598-31-2 YesY
PubChem 11715
ChemSpider 11223 YesY
ChEBI CHEBI:51845 YesY
RTECS number UC0525000
Jmol-3D images Image 1
Properties
Molecular formula C3H5BrO
Molar mass 136.98 g mol−1
Appearance Colorless lachrymator
Density 1.634 g/cm³
Melting point

-36.5 °C, 237 K, -34 °F

Boiling point

137 °C, 410 K, 279 °F

Vapor pressure 1.1 kPa (20 °C)
Hazards
MSDS MSDS at ILO
Flash point 51.1 °C
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bromoacetone is an organic compound with the formula CH3COCH2Br. This colorless liquid is a lachrymatory agent. It is a precursor to other organic compounds.

Occurrence

Bromoacetone is naturally present (less than 1%) in the essential oil of a seaweed from the vicinity of the Hawaiian Islands.[2]

Synthesis

Bromoacetone is available commercially, sometimes stabilized with magnesium oxide. It was first described in the 19th century, attributed to N. Sokolowsky.[3]

Bromoacetone is prepared by combining bromine and acetone,[4] with catalytic acid. If you use a base you will obtain bromoform instead. CH3C(O)CH3 + Br2 → CH3C(O)CH2Br + HBr The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. In terms of mechanism, as with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine.[5]

Applications

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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.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 a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone (b.p. 40–43°/12 mm, CAS #116-09-6).[6]

See also

References

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