Bromoacetone
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| Bromoacetone | |
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| 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] |
| PubChem | |
| RTECS number | UC0525000 |
| SMILES | CC(=O)CBr |
| InChI | 1/C3H5BrO/c1-3(5)2-4/h2H2,1H3 |
| Properties | |
| Molecular formula | C3H5BrO |
| Molar mass | 136.99 g/mol |
| Appearance | Colorless lachrymator |
| Density | 1.634 g/cm³ |
| Melting point |
-36.5 °C |
| Boiling point |
137 °C |
| Vapor pressure | 1.1 kPa (20 °C) |
| Hazards | |
| Flash point | 51.1 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Bromoacetone is a chemical compound with the formula CH3COCH2Br. This colorless liquid is a lachrymatory agent. It is a precursor to other organic compounds.
Bromoacetone was first prepared in the 19th century.[1] 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 Due to its toxicity, it is obsolete as a riot control agent and is not used anymore.
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[edit] Occurrence
Bromoacetone is naturally present (less than 1%) in the essential oil of a seaweed from the vicinity of the Hawaiian Islands.[2] In atmosphere it is degraded by the photochemically produced hydroxyl radicals.
[edit] Synthesis
Bromoacetone is available commercially, sometimes stabilized with magnesium oxide.
Bromoacetone is prepared by reacting bromine and acetone,[3] with catalytic acid or base.
- CH3C(O)CH3 + Br2 → CH3C(O)CH2Br + HBr
As with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine.[4] The main difficulty with this method is over-bromination, resulting in di- and tribrominated products.
[edit] Applications
Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone (b.p. 35–47°/12 mm, CAS #116-09-6).[5]
[edit] See also
[edit] References
- ^ Sokolowsky, Berichte volume 9, pp. 1687 (1876).
- ^ B. Jay Burreson, Richard E. Moore, and Peter P. Roller (1976). "Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta)". Journal of Agricultural and Food Chemistry 24 (4): 856–861. doi:.
- ^ Levene, P. A. (1943). "Bromoacetone". Org. Synth.; Coll. Vol. 2: 88.
- ^ William Reusch. Carbonyl Reactivity. VirtualText of Organic Chemistry. Retrieved on 2007-10-27.
- ^ Levene, P. A.; Walti, A. (1943). "Acetol". Org. Synth.; Coll. Vol. 2: 5.
- Merck Index, 11th Edition, 1389
