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Dichloroacetyl chloride

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Dichloroacetyl chloride
Names
Preferred IUPAC name Dichloroacetyl chloride
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1209426
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.091 Edit this at Wikidata
EC Number
  • 201-199-9
Gmelin Reference 430743
KEGG
PubChem CID
RTECS number
  • AO6650000
UNII
UN number 1765
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2HCl3O/c3-1(4)2(5)6/h1HKey: FBCCMZVIWNDFMO-UHFFFAOYSA-N
SMILES
  • C(C(=O)Cl)(Cl)Cl
Properties
Chemical formula C2HCl3O
Molar mass 147.38 g·mol
Appearance colorless fuming liquid
Density 1.5315 g/cm
Boiling point 107 °C (225 °F; 380 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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:

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.

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

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. ISBN 978-3527306732.
  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.
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