Dichloroacetyl chloride

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-199-9
430743
KEGG
PubChem CID
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
Appearancecolorless 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]

Contents

Preparation

Unlike typical acid chlorides, which are often prepared from the associated carboxylic acid, dichloroacetyl chloride is not prepared from dichloroacetic acid. Instead, 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

It is a precursor to various herbicides including dichlormid. [5]

Hydrolysis gives dichloroacetic acid. It is one of the precursors to antibiotics, including chloramphenicol.

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References

  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.
  5. Riechers, Dean E.; Kreuz, Klaus; Zhang, Qin (2010). "Detoxification without Intoxication: Herbicide Safeners Activate Plant Defense Gene Expression". Plant Physiology. 153 (1): 3–13. doi:10.1104/pp.110.153601. PMC   2862420 . PMID   20237021.