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

Hexachloroacetone
Names
Preferred IUPAC name 1,1,1,3,3,3-Hexachloropropan-2-one
Other names perchloroacetone HCA
Identifiers
CAS Number	116-16-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82243
ChEMBL	ChEMBL3182582
ChemSpider	13873693 Y
ECHA InfoCard	100.003.754
EC Number	204-129-5
KEGG	C19122 Y
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 Y Key: DOJXGHGHTWFZHK-UHFFFAOYSA-N Y 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/cm3[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). N verify (what is YN ?) Infobox references

Reactions and uses

Hexachloroacetone functions equivalently to trichloroacetyl chloride, i.e. as an trichloroacetylating agent.^[2]

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:^[3]

(CCl₃)₂CO + 6 HF → (CF₃)₂CO + 6 HCl

See also

• Chloroacetone
• Dichloroacetone