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| Names | |
|---|---|
| IUPAC nameExpression error: Unexpected > operator.
1-Bromoacetone
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| 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
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598-31-2 
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| ChEBI | CHEBI:51845
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| ChEMBL | ChEMBL1085947
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| ChemSpider | 11223
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| Jmol 3D model | Interactive image |
| PubChem | 11715 |
| RTECS number | UC0525000 |
InChI
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SMILES
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| Properties | |
Chemical formula
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C3H5BrO |
| Molar mass | 136.98 g·mol−1 |
| Appearance | Colorless lachrymator |
| Density | 1.634 g/cm³ |
| Melting point | |
| Boiling point | |
| Vapor pressure | 1.1 kPa (20 °C) |
| Hazards | |
| Flash point | |
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] 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[]
- ↑ Merck Index, 11th Edition, 1389
- ↑ Burreson, B. J.; Moore, R. E.; Roller, P. P. (1976). "Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta)". pp. 856–861. Digital object identifier:10.1021/jf60206a040.
- ↑ Wagner, G. (1876). "Sitzung der russischen chemischen Gesellschaft am 7./19. October 1876". pp. 1687–1688. Digital object identifier:10.1002/cber.187600902196. http://gallica.bnf.fr/ark:/12148/bpt6k906830/f657.image.langEN.
- ↑ "Bromoacetone". 1930. pp. 12. http://www.orgsyn.org/demo.aspx?prep=cv2p0088.; "Coll. Vol.". pp. 88.
- ↑ Reusch, W. (2013-05-05). "Carbonyl Reactivity". Virtual Textbook of Organic Chemistry. Michigan State University. http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm.
- ↑ "Acetol". 1930. pp. 1. http://www.orgsyn.org/demo.aspx?prep=cv2p0005.; "Coll. Vol.". pp. 5.
The original article can be found at Bromoacetone and the edit history here.