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 Due to its toxicity, it is obsolete as a [[riot control agent]] and is not used anymore.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]] [[de:Bromaceton]] [[pl:Bromoaceton]]