Hexachloroacetone

Hexachloroacetone is an organic compound with the formula (Cl₃C)₂CO. It is also called hexachloropropanone or perchloroacetone. Numbers indicating the position of the chlorine-atoms are generally omitted as all the possible positions are substituted with chlorine. It is a colorless liquid, slightly soluble in water.

Hexachloroacetone

Names
IUPAC name 1,1,1,3,3,3-hexachloropropanone
Other names perchloroacetone HCA
Identifiers
CAS Number	116-16-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82243
ChEMBL	ChEMBL3182582
ChemSpider	13873693
ECHA InfoCard	100.003.754
EC Number	204-129-5
KEGG	C19122
PubChem CID	8303
RTECS number	UC2100000
UNII	RU0LGU279Y
UN number	2661
CompTox Dashboard (EPA)	DTXSID7021601
InChI InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 Key: DOJXGHGHTWFZHK-UHFFFAOYSA-N InChI=1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 Key: DOJXGHGHTWFZHK-UHFFFAOYAW
SMILES ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
Properties
Chemical formula	C3Cl6O
Molar mass	264.75 g/mol
Density	1.7434 g/cm^3[1]
Melting point	−2 °C (28 °F; 271 K)
Boiling point	204 °C (399 °F; 477 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The main use of hexachloroacetone is as a pesticide. For the use of hexachloroacetone in the preparation of a novel insect repellent see Perkow reaction. The industrial route to hexafluoroacetone involves treatment of hexachloroacetone with HF:[2]

(CCl₃)₂CO + 6 HF → (CF₃)₂CO + 6 HCl

See also

• Chloroacetone
• Dichloroacetone

References

1. CRC Handbook of Chemistry and Physics, Internet Version, CRC Press (2005)
2. Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 3527306730.CS1 maint: uses authors parameter (link)