Hexachloroacetone

Structural formula
General
Surname	Hexachloroacetone
other names	1,1,1,3,3,3-hexachloro-2-propanone ( IUPAC )
Molecular formula	C 3 Cl 6 O
Brief description	colorless liquid
External identifiers / databases
EC number	204-129-5
ECHA InfoCard	100.003.754
PubChem	8303
ChemSpider	13873693
Wikidata	Q10860983
properties
Molar mass	264.75 g mol −1
Physical state	liquid
density	1.74 g cm −3
Melting point	−3 ° C
boiling point	203-205 ° C; 66-70 ° C (6 mmHg );
Vapor pressure	0.29 hPa (20 ° C)
solubility	slightly soluble in water (17.5 g l −1 at 20 ° C); soluble in acetone;
Refractive index	1.511 (20 ° C)
safety instructions
H and P phrases	H: 302-331-317-411
	P: 261-280-301 + 312 + 330-304 + 340-311-403 + 233
Toxicological data	1550 mg kg −1 ( LD 50 , rat , oral ) ; 2980 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Hexachloroacetone is a chemical compound from the group of ketones .

Extraction and presentation

Hexachloroacetone, by chlorination of isopropyl alcohol are obtained at 70-100 ° C, whereby 1,1,1,3,3-pentachloropropane acetone is formed, or by chlorination of chloroacetone in the presence of acetic acid .

properties

Hexachloroacetone is a flammable, hardly inflammable, colorless liquid that is sparingly soluble in water. It decomposes when heated, which can produce chlorine , hydrogen chloride , phosgene and dioxins .

use

Hexachloroacetone is used for the chlorination of enamines , for the production of trichloroacetamides and trichloroacetates under neutral conditions and as a starting material for the production and cycloaddition of oxyallyl intermediates. It was also used as a herbicide in the past .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Hexachloro-2-propanone, produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC) at Sigma-Aldrich , accessed on November 24, 2019 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on hexachloroacetone in the GESTIS substance database of the IFA , accessed on November 24, 2019(JavaScript required) .
↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 302 ( limited preview in Google Book search).
↑ Entry on hexachloroacetone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 24, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry on hexachloroacetone in the Hazardous Substances Data Bank , accessed on November 24, 2019.
^ Houben-Weyl Methods of Organic Chemistry Vol. V / 3, 4th Edition Fluorine and Chlorine Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-179994-3 , p. 616 ( limited preview in Google Book search).
↑ Richard Wegler: Chemistry of pesticides and pesticides Volume 2: Fungicides · Herbicides · Natural · Plant growth substances · Residue problems . Springer-Verlag, 2013, ISBN 978-3-7091-4184-7 , pp. 204 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Hexachloro-2-propanone, produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC) at Sigma-Aldrich , accessed on November 24, 2019 ( PDF ).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on hexachloroacetone in the GESTIS substance database of the IFA , accessed on November 24, 2019(JavaScript required) .

[David_R._Lide-3] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 302 ( limited preview in Google Book search).

[CLP_100.003.754-4] Entry on hexachloroacetone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 24, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[HSDB-5] Entry on hexachloroacetone in the Hazardous Substances Data Bank , accessed on November 24, 2019.

[6] Houben-Weyl Methods of Organic Chemistry Vol. V / 3, 4th Edition Fluorine and Chlorine Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-179994-3 , p. 616 ( limited preview in Google Book search).

[7] Richard Wegler: Chemistry of pesticides and pesticides Volume 2: Fungicides · Herbicides · Natural · Plant growth substances · Residue problems . Springer-Verlag, 2013, ISBN 978-3-7091-4184-7 , pp. 204 ( limited preview in Google Book search).