Chloroacetone

{{chembox | Watchedfields = changed | verifiedrevid = 443518079 | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Chloroacetone 2D skeletal.svg | ImageSize = 130px | ImageFile1 = Chloroacetone-3D-balls.png | ImageSize1 = 150px | PIN = 1-Chloropropan-2-one | OtherNames =Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane UN 1695 |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6323 | InChIKey = BULLHNJGPPOUOX-UHFFFAOYAY | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BULLHNJGPPOUOX-UHFFFAOYSA-N | CASNo = 78-95-5 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6571 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 60ZTR74268 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 47220 | SMILES = ClCC(=O)C | RTECS = UC0700000 | EINECS = 201-161-1 | Beilstein = 605369 }} |Section2={{Chembox Properties | C=3 | H=5 | Cl=1 | O=1 | Appearance = Colorless liquid, oxidizes to amber | Density = 1.123 g/cm3 | MeltingPtC = -44.5 | BoilingPtC = 119 | Solubility = 10 g/100 mL at 20 °C | SolubleOther = miscible with alcohol, ether, chloroform | VaporPressure = 1.5 kPa | Dipole = 2.36 | MagSus = −50.9·10−6 cm3/mol }} |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPtC = 35 | AutoignitionPtC = 610 | ExploLimits = 3.4% - ?<ref name="cdc">{{cite web | title=ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH | url=https://www.cdc.gov/niosh/ipcsneng/neng0760.html | publisher= Center for Disease Control| date=2006-10-11 | access-date=2009-04-17}}</ref> | LD50 = 100 mg/kg (rats, oral)<ref name="chw"/> | PEL = }} |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = }} }}

'''Chloroacetone''' is a liquid, a chemical compound with the formula {{chem2|CH3COCH2Cl|auto=1}}. Regulated for its potential as a tear gas, it is primarily a chemical intermediate in commerce.

==Properties== At STP it is a colorless liquid with a pungent odor.<ref name=ohsa>{{cite web | url = http://www.osha.gov/SLTC/healthguidelines/chloroacetone/recognition.html | title = Occupational Safety and Health Guideline for Chloroacetone | access-date = 2008-06-06 | publisher = U.S. Department of Labor - Occupational Safety & Health Administration | archive-url = https://web.archive.org/web/20130503155817/http://www.osha.gov/SLTC/healthguidelines/chloroacetone/recognition.html | archive-date = 2013-05-03 | url-status = dead }}</ref> On exposure to light, it turns to a dark yellow-amber color.<ref name=ipcs>{{cite web | url = http://www.inchem.org/documents/icsc/icsc/eics0760.htm | title= CHLOROACETONE | access-date = 2008-06-06 | publisher = International Programme on Chemical Safety}}</ref> It was used as a tear gas in World War I.<ref>{{cite book | first=Ludwig Fritz | last=Haber | year=1986 | title=The Poisonous Cloud: Chemical Warfare in the First World War | publisher=Oxford University Press | isbn=0-19-858142-4 }}</ref>

==Synthesis== Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone.

==Applications== Chloroacetone is primarily an intermediate in chemical manufacture. In the early 2000s, it was used to make dye couplers for colour film photography.<ref name="chw"> {{Cite book | last1 =Hathaway | first1 =Gloria J. | last2 =Proctor | first2 =Nick H. | year = 2004 | title =Proctor and Hughes' Chemical Hazards of the Workplace | edition =5 | publisher = Wiley-Interscience | pages = 143–144 | isbn =978-0-471-26883-3 | url= https://books.google.com/books?id=y3-Ef3y53PkC&dq=Chloroacetone&pg=PA143 | access-date = 2009-04-16 }}</ref> In the pharmaceutical industry, it is a precursor to phenoxyacetone.<ref name="HurdPerletz1946">{{cite journal|last1=Hurd|first1=Charles D.|last2=Perletz|first2=Percy|title=Aryloxyacetones1|journal=Journal of the American Chemical Society|volume=68|issue=1|year=1946|pages=38–40|issn=0002-7863|doi=10.1021/ja01205a012}}</ref>

It is also used in the Feist-Benary synthesis of furans:<ref name="nrhc"> {{Cite book | last1 =Li | first1 =Jie-Jack | last2 =Corey | first2 =E. J. | year = 2004 | title =Name Reactions in Heterocyclic Chemistry | publisher = Wiley-Interscience | pages = 160 | isbn =978-0-471-30215-5 | url= https://books.google.com/books?id=1N-MZVSesTcC&dq=Chloroacetone&pg=PA160 | access-date = 2009-04-16 }}</ref> : 400px

==Purification== Chloroacetone purchased from commercial suppliers contains 5% impurities including mesityl oxide, which is not removed by distillation. Mesityl oxide can be oxidized using acidified KMnO4 to form a diol (followed by separation with ether), which is removed on subsequent distillation.<ref>Phys. Chem. Chem. Phys., 2000,2, 237-245</ref>

==Transportation regulations== Transportation of unstabilized chloroacetone has been banned in the United States by the US Department of Transportation. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its UN number is 1695.

==References== {{reflist}}

==External links== * [https://web.archive.org/web/20100621055908/http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm The Halogenation of Carbonyls]

Category:Organochlorides Category:Lachrymatory agents Category:Chemical weapons in World War I Category:Ketones