Chloroacetone
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| Watchedfields = changed
| verifiedrevid = 443518079
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| 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
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|Section7={{Chembox Hazards
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| FlashPtC = 35
| AutoignitionPtC = 610
| LD50 = 100 mg/kg (rats, oral)
| PEL = }}
|Section8={{Chembox Related
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Chloroacetone is a chemical compound with the formula {{chem2|CH3COCH2Cl|auto=1}}. At STP it is a colorless liquid with a pungent odor.{{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 }} On exposure to light, it turns to a dark yellow-amber color.{{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}} It was used as a tear gas in World War I.{{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 }}
Synthesis
Applications
Chloroacetone is used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing.
{{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
}} It is also used in the Feist-Benary synthesis of furans.
{{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
}}
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- Reaction of phenoxide with chloroacetone gives phenoxyacetone,{{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}} which is used to make a wide variety of different pharmaceuticals. A catalytic amount of potassium iodide is also necessary to facilitate a Finkelstein reaction.
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.Phys. Chem. Chem. Phys., 2000,2, 237-245
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.
See also
References
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External links
- [https://web.archive.org/web/20100621055908/http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm The Halogenation of Carbonyls]
{{Chemical agents}}
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