Hexachloroacetone

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

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.

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

References

1. CRC Handbook of Chemistry and Physics, Internet Version, CRC Press (2005)
2. Bernard Sukornick (1960). "α,α,α-Trichloroacetanilide". Organic Syntheses. 40: 103. doi:10.15227/orgsyn.040.0103.
3. Günter Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN   3-527-30673-0.