Bromoacetone

Bromoacetone^[1]

Names
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
CAS Number	598-31-2
ChEBI	CHEBI:51845
ChEMBL	ChEMBL1085947
ChemSpider	11223
IUPHAR/BPS	6293
Jmol 3D model	Interactive image
PubChem	11715
RTECS number	UC0525000
InChI InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3 Key: VQFAIAKCILWQPZ-UHFFFAOYSA-N InChI=1/C3H5BrO/c1-3(5)2-4/h2H2,1H3 Key: VQFAIAKCILWQPZ-UHFFFAOYAC
SMILES BrCC(=O)C
Properties
Chemical formula	C3H5BrO
Molar mass	136.98 g·mol^−1
Appearance	Colorless lachrymator
Density	1.634 g/cm^3
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

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]

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

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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.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

• Use of poison gas in World War I

References

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