Bromoacetone
3133571
224463555
2008-07-08T23:14:52Z
Schoschie
4361369
{{Chembox new
| ImageFile = Bromoacetone.png
| ImageSize = 120px
| IUPACName = 1-Bromoacetone
| OtherNames = Bromoacetone<br/> 1-Bromo-2-propanone<br/> α-Bromoacetone<br/> Acetonyl bromide<br/> Acetyl methyl bromide<br/> Bromomethyl methyl ketone<br/> Monobromoacetone<br/> Martonite<br/> BA<br/> UN 1569
| Section1 = {{Chembox Identifiers
| CASNo = 598-31-2
| PubChem = 11715
| SMILES = CC(=O)CBr
| InChI = 1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
| RTECS = UC0525000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>5</sub>BrO
| MolarMass = 136.99 g/mol
| Appearance = Colorless lachrymator
| Density = 1.634 g/cm³
| MeltingPt = -36.5 °C
| BoilingPt = 137 °C
| Solubility =
| VaporPressure = 1.1 kPa (20 °C)
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt = 51.1 °C
| Autoignition =
}}
}}
'''Bromoacetone''' is a [[chemical compound]] with the [[chemical formula|formula]] {{Carbon}}{{Hydrogen}}<sub>3</sub>C{{Oxygen}}CH<sub>2</sub>{{Bromine}}. This colorless liquid is a [[lachrymatory agent]]. It is a precursor to other [[organic compound]]s.
Bromoacetone was first prepared in the 19th century.<ref>Sokolowsky, Berichte volume 9, pp. 1687 (1876).</ref> 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 Due to its toxicity, it is obsolete as a [[riot control agent]] and is not used anymore.
==Occurrence==
Bromoacetone is naturally present (less than 1%) in the [[essential oil]] of a [[seaweed]] from the vicinity of the [[Hawaiian Islands]].<ref>{{cite journal
| title = Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta)
| author = B. Jay Burreson, Richard E. Moore, and Peter P. Roller
| journal = Journal of Agricultural and Food Chemistry
| pages = 856–861
| doi = 10.1021/jf60206a040
| volume = 24
| issue = 4
| year = 1976}}</ref> In atmosphere it is degraded by the photochemically produced [[hydroxyl]] [[radical (chemistry)|radicals]].
==Synthesis==
Bromoacetone is available commercially, sometimes stabilized with [[magnesium oxide]].
Bromoacetone is prepared by reacting [[bromine]] and [[acetone]],<ref>{{OrgSynth | author = Levene, P. A. | title = Bromoacetone | collvol = 2 | collvolpages = 88 | year = 1943 | prep = cv2p0088}}</ref> with catalytic acid or base.
:CH<sub>3</sub>C(O)CH<sub>3</sub> + Br<sub>2</sub> → CH<sub>3</sub>C(O)CH<sub>2</sub>Br + HBr
As with all ketones, acetone [[enol]]izes in the presence of acids or bases. The alpha carbon then undergoes [[electrophilic substitution]] with bromine.<ref>{{cite web | title = Carbonyl Reactivity | work = VirtualText of Organic Chemistry | author = William Reusch | url = http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | accessdate = 2007-10-27}}</ref> The main difficulty with this method is over-bromination, resulting in di- and tribrominated products.
==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).<ref>{{OrgSynth | author = Levene, P. A.; Walti, A. | title = Acetol | collvol = 2 | collvolpages = 5 | year = 1943 | prep = cv2p0005}}</ref>
==See also==
*[[Use of poison gas in World War I]]
==References==
<references/>
*''Merck Index'', 11th Edition, '''1389'''
==External links==
* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1074.pdf MSDS at ilo.org]
[[Category:Organobromides]]
[[Category:Lachrymatory agents]]
[[Category:World War I weapons]]
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