Bromoacetone

Bromoacetone[1]
IUPAC name 1-Bromoacetone
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 Y
PubChem	11715
ChemSpider	11223 Y
ChEBI	CHEBI:51845 Y
ChEMBL	CHEMBL1085947 Y
RTECS number	UC0525000
Jmol-3D images	Image 1
SMILES BrCC(=O)C
InChI InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3 Y Key: VQFAIAKCILWQPZ-UHFFFAOYSA-N Y InChI=1/C3H5BrO/c1-3(5)2-4/h2H2,1H3 Key: VQFAIAKCILWQPZ-UHFFFAOYAC
Properties
Molecular formula	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
MSDS	MSDS at ILO
Flash point	51.1 °C; 124.0 °F; 324.2 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.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

• 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: 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: 5