bromoacetone
{{chembox
| Watchedfields = changed
| Reference=Merck Index, 11th Edition, 1389
| verifiedrevid = 443428893
| ImageFile = bromoaceton.svg
| ImageSize = 160
| ImageAlt = Skeletal formula
| ImageFile1 = Bromoacetone-3D-balls.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model
| PIN = 1-Bromopropan-2-one
| OtherNames = Bromoacetone
1-Bromo-2-propanone
α-Bromoacetone
Acetonyl bromide
Acetyl methyl bromide
Bromomethyl methyl ketone
Monobromoacetone
Martonite
BA
UN 1569
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 6293
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11223
| InChIKey = VQFAIAKCILWQPZ-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1085947
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VQFAIAKCILWQPZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 598-31-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3O8L0EWR5Q
| PubChem = 11715
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51845
| SMILES = BrCC(=O)C
| InChI = 1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
| RTECS = UC0525000
}}
|Section2={{Chembox Properties
| C=3 | H=5 | Br=1 | O=1
| Appearance = Colorless liquid
| Density = 1.634 g/cm3
| MeltingPtC = -36.5
| BoilingPtC = 137
| Solubility =
| VaporPressure = 1.1 kPa (20 °C)
}}
|Section3={{Chembox Hazards
| ExternalSDS = [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1074.pdf MSDS at ILO]
| FlashPtC = 51.1
| AutoignitionPtC =
}}
}}
Bromoacetone is an organic compound with the formula {{chem2|auto=1|CH3COCH2Br}}. It is a colorless liquid although impure samples appear yellow or even brown. It is a lachrymatory agent and a precursor to other organic compounds.
Occurrence in nature
Bromoacetone is present (less than 1%) in the essential oil of a seaweed (Asparagopsis taxiformis) from the vicinity of the Hawaiian Islands.{{cite journal |author1=Burreson, B. J. |author2=Moore, R. E. |author3=Roller, P. P. | title = Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta) | journal = Journal of Agricultural and Food Chemistry | year = 1976 | volume = 24 | issue = 4 | pages = 856–861 | doi = 10.1021/jf60206a040}}
Synthesis
Bromoacetone is available commercially, sometimes stabilized with magnesium oxide. It was first described in the 19th century, attributed to N. Sokolowsky.{{cite journal | author = Wagner, G. | title = Sitzung der russischen chemischen Gesellschaft am 7./19. October 1876 | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1876 | volume = 9 | issue = 2 | pages = 1687–1688 | doi = 10.1002/cber.187600902196 | url = http://gallica.bnf.fr/ark:/12148/bpt6k906830/f657.image.langEN| url-access = subscription }}
File:Bromoacetone Synthesis V.1.svg
Bromoacetone is prepared by combining bromine and acetone,{{OrgSynth | author = Levene, P. A. | title = Bromoacetone | year = 1930 | volume = 10 | pages = 12 | collvol = 2 | collvolpages = 88 | prep = cv2p0088}} with catalytic acid. As with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. If a base is present, bromoform is obtained instead, by the haloform reaction.{{cite web | title = Carbonyl Reactivity | work = Virtual Textbook of Organic Chemistry | author = Reusch, W. | url = http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | date = 2013-05-05 | publisher = Michigan State University | access-date = 2007-10-27 | archive-url = https://web.archive.org/web/20100621055908/http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | archive-date = 2010-06-21 | url-status = dead}}
Applications
It was used in World War I as a chemical weapon, called BA by British and B-Stoff (Weisskreuz) by Germans. Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone by reaction with aqueous sodium hydroxide.{{OrgSynth | author = Levene, P. A. |author2=Walti, A. | title = Acetol | year = 1930 | volume = 10 | pages = 1 | collvol = 2 | collvolpages = 5 | prep = cv2p0005 }}
==See also==