{{chembox | Verifiedfields = changed | verifiedrevid = 400104186 | Name = Hexachloroacetone | ImageFile = Hexachloroacetone.png | ImageSize = 170px | ImageName = Hexachloroacetone | ImageFile1 = Hexachloroacetone-3D-balls.png | ImageSize1 = 170px | PIN = 1,1,1,3,3,3-Hexachloropropan-2-one | OtherNames = perchloroacetone<br />HCA | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 13873693 | InChI = 1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 | InChIKey = DOJXGHGHTWFZHK-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DOJXGHGHTWFZHK-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 116-16-5 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C19122 | ChEBI = 82243 | ChEMBL = 3182582 | EINECS = 204-129-5 | PubChem = 8303 | RTECS = UC2100000 | UNNumber = 2661 | UNII = RU0LGU279Y | SMILES = ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl }} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>Cl<sub>6</sub>O | MolarMass = 264.75 g/mol | Density = 1.7434 g/cm<sup>3</sup><ref>''CRC Handbook of Chemistry and Physics'', Internet Version, CRC Press (2005)</ref> | MeltingPtC = -2 | BoilingPtC = 204 }} }}
'''Hexachloroacetone''' is an organic compound with the formula (Cl<sub>3</sub>C)<sub>2</sub>CO. 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 a trichloroacetylating agent.<ref>{{cite journal |doi=10.15227/orgsyn.040.0103|author=Bernard Sukornick|title=α,α,α-Trichloroacetanilide|journal=Organic Syntheses|year=1960|volume=40|page=103}}</ref>
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:<ref name=Ullmanns>{{cite encyclopedia|author=Günter Siegemund |author2=Werner Schwertfeger |author3=Andrew Feiring |author4=Bruce Smart |author5=Fred Behr |author6=Herward Vogel |author7=Blaine McKusick |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a11_349|chapter=Fluorine Compounds, Organic|isbn=3-527-30673-0}}</ref> :(CCl<sub>3</sub>)<sub>2</sub>CO + 6 HF → (CF<sub>3</sub>)<sub>2</sub>CO + 6 HCl
==See also== * Chloroacetone * Dichloroacetone
==References== {{reflist}}
==Links== *{{PPDB|2797}}
Category:Trichloromethyl compounds Category:Ketones Category:Pesticides
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