Dichloroacetyl chloride

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Dichloroacetyl chloride
2,2-dichlooracetylchloride.png
Names
Preferred IUPAC name
Dichloroacetyl chloride
Identifiers
3D model (JSmol)
1209426
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.091 Edit this at Wikidata
EC Number
  • 201-199-9
430743
KEGG
RTECS number
  • AO6650000
UNII
UN number 1765
  • InChI=1S/C2HCl3O/c3-1(4)2(5)6/h1H
    Key: FBCCMZVIWNDFMO-UHFFFAOYSA-N
  • C(C(=O)Cl)(Cl)Cl
Properties
C2HCl3O
Molar mass 147.38 g·mol−1
Appearance colorless fuming liquid
Density 1.5315 g/cm3
Boiling point 107 °C (225 °F; 380 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichloroacetyl chloride is the organic compound with the formula CHCl2COCl. It is the acyl chloride of dichloroacetic acid.[1] It is a colourless liquid and is used in acylation reactions.[2][3]

Preparation[edit]

Unlike typical acid chlorides, dichloroacetyl chloride is not prepared from the acid. Industrial routes include oxidation of 1,1,2-trichloroethane, hydrolysis of pentachloroethane, and the carboxylation of chloroform:[4]

CHCl2CH2Cl + O2 → CHCl2COCl + H2O
CHCl2CCl3 + H2O → CHCl2COCl + 2 HCl
CHCl3 + CO2 → CHCl2COCl + 1/2 O2

Uses[edit]

Hydrolysis gives dichloroacetic acid. It is one of the precursors to antibiotics, including chloramphenicol. Another reported use was in the synthesis of WIN 18,446.[citation needed]

References[edit]

  1. ^ "Pubchem". Pubchem. Retrieved 1 July 2017.
  2. ^ Richard P. Pohanish; Stanley A. Greene (25 August 2009). Wiley Guide to Chemical Incompatibilities. John Wiley & Sons. pp. 327–8. ISBN 978-0-470-52330-8.
  3. ^ Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 26: Ketones. Georg Thieme Verlag. 14 May 2014. pp. 759–60. ISBN 978-3-13-172011-5.
  4. ^ Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537.