Chloroacetone

Chloroacetone is a chemical compound with the formula CH₃COCH₂Cl. At STP it is a colorless liquid with a pungent odor.^[3] On exposure to light, it turns to a dark yellow-amber color.^[4] It was used as a tear gas in World War I.^[5]

Chloroacetone

Names
Preferred IUPAC name 1-Chloropropan-2-one
Other names Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane UN 1695
Identifiers
CAS Number	78-95-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605369
ChEBI	CHEBI:47220 Y
ChemSpider	6323 Y
ECHA InfoCard	100.001.056
EC Number	201-161-1
PubChem CID	6571
RTECS number	UC0700000
UNII	60ZTR74268 Y
CompTox Dashboard (EPA)	DTXSID0021547
InChI InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 Y Key: BULLHNJGPPOUOX-UHFFFAOYSA-N Y Key: BULLHNJGPPOUOX-UHFFFAOYAY
SMILES ClCC(=O)C
Properties
Chemical formula	C3H5ClO
Molar mass	92.52 g·mol−1
Appearance	Colorless liquid, oxidizes to amber
Density	1.123 g/cm3
Melting point	−44.5 °C (−48.1 °F; 228.7 K)
Boiling point	119 °C (246 °F; 392 K)
Solubility in water	10 g/100 mL at 20 °C
Solubility	miscible with alcohol, ether, chloroform
Vapor pressure	1.5 kPa
Magnetic susceptibility (χ)	-50.9·10−6 cm3/mol
Dipole moment	2.36
Hazards
Flash point	35 °C (95 °F; 308 K)
Autoignition temperature	610 °C (1,130 °F; 883 K)
Explosive limits	3.4% - ?[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	100 mg/kg (rats, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Synthesis

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

Applications

Chloroacetone is used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing.^[2] It is also used in the Feist-Benary synthesis of furans.^[6]

• Reaction of phenoxide with chloroacetone gives phenoxyacetone,^[7] 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.^[8]

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

• Bromoacetone
• Dichloroacetone
• Fluoroacetone
• Hexachloroacetone
• Use of poison gas in World War I

References

1. "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. Retrieved 2009-04-17.
2. Hathaway, Gloria J.; Proctor, Nick H. (2004). Proctor and Hughes' Chemical Hazards of the Workplace (5 ed.). Wiley-Interscience. pp. 143–144. ISBN 978-0-471-26883-3. Retrieved 2009-04-16.
3. "Occupational Safety and Health Guideline for Chloroacetone". U.S. Department of Labor - Occupational Safety & Health Administration. Archived from the original on 2013-05-03. Retrieved 2008-06-06.
4. "CHLOROACETONE". International Programme on Chemical Safety. Retrieved 2008-06-06.
5. Haber, Ludwig Fritz (1986). The Poisonous Cloud: Chemical Warfare in the First World War. Oxford University Press. ISBN 0-19-858142-4.
6. Li, Jie-Jack; Corey, E. J. (2004). Name Reactions in Heterocyclic Chemistry. Wiley-Interscience. p. 160. ISBN 978-0-471-30215-5. Retrieved 2009-04-16.
7. Hurd, Charles D.; Perletz, Percy (1946). "Aryloxyacetones1". Journal of the American Chemical Society. 68 (1): 38–40. doi:10.1021/ja01205a012. ISSN 0002-7863.
8. Phys. Chem. Chem. Phys., 2000,2, 237-245

External links

• The Halogenation of Carbonyls