Bromoacetone

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Bromoacetone[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1-Bromopropan-2-one
Other names
Bromoacetone
1-Bromo-2-propanone
α-Bromoacetone
Acetonyl bromide
Acetyl methyl bromide
Bromomethyl methyl ketone
Monobromoacetone
Martonite
BA
UN 1569
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.027
RTECS number UC0525000
Properties
C3H5BrO
Molar mass 136.98 g·mol−1
Appearance Colorless lachrymator
Density 1.634 g/cm3
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)
Hazards
Safety data sheet MSDS at ILO
Flash point 51.1 °C (124.0 °F; 324.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[edit]

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

Synthesis[edit]

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

Acetone and bromine form bromoacetone.

Bromoacetone is prepared by combining bromine and acetone,[4] 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, via the haloform reaction.[5]

Applications[edit]

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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.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.[6]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 1389
  2. ^ Burreson, B. J.; Moore, R. E.; Roller, P. P. (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. ^ Wagner, G. (1876). "Sitzung der russischen chemischen Gesellschaft am 7./19. October 1876". Berichte der Deutschen Chemischen Gesellschaft. 9 (2): 1687–1688. doi:10.1002/cber.187600902196. 
  4. ^ Levene, P. A. (1930). "Bromoacetone". Org. Synth. 10: 12. ; Coll. Vol., 2, p. 88 
  5. ^ Reusch, W. (2013-05-05). "Carbonyl Reactivity". Virtual Textbook of Organic Chemistry. Michigan State University. 
  6. ^ Levene, P. A.; Walti, A. (1930). "Acetol". Org. Synth. 10: 1. ; Coll. Vol., 2, p. 5