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 ;
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/cm3
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). verify (what is ?) 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

References

^ CRC Handbook of Chemistry and Physics, Internet Version, CRC Press (2005)
^ Bernard Sukornick (1960). "α,α,α-Trichloroacetanilide". Organic Syntheses. 40: 103. doi:10.15227/orgsyn.040.0103.
^ 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.

Links

Hexachloroacetone in the Pesticide Properties DataBase (PPDB)

[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.

[Ullmanns-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.

[1]

[2]

[3]

Reactions and uses

See also

References

Links