Wikipedia

Bromoacetone

Bromoacetone is an organic compound with the formula CH3COCH2Br. It is a colorless liquid although impure samples appear yellow or even brown. It is a lachrymatory agent and a precursor to other organic compounds.

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 (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.027 Edit this at Wikidata
RTECS number
  • UC0525000
UNII
  • InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3 checkY
    Key: VQFAIAKCILWQPZ-UHFFFAOYSA-N checkY
  • InChI=1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
    Key: VQFAIAKCILWQPZ-UHFFFAOYAC
  • BrCC(=O)C
Properties
C3H5BrO
Molar mass 136.976 g·mol−1
Appearance Colorless liquid
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
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).
checkY verify (what is checkY☒N ?)

Occurrence in nature

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

Synthesis

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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, by the haloform reaction.[5]

Applications

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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.[6]

See also

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References

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  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". Organic Syntheses. 10: 12; Collected Volumes, vol. 2, p. 88.
  5. ^ Reusch, W. (2013-05-05). "Carbonyl Reactivity". Virtual Textbook of Organic Chemistry. Michigan State University. Archived from the original on 2010-06-21. Retrieved 2007-10-27.
  6. ^ Levene, P. A.; Walti, A. (1930). "Acetol". Organic Syntheses. 10: 1; Collected Volumes, vol. 2, p. 5.
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