Dichloroacetyl chloride explained

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

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.^[4]

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

Notes and References

1. Web site: Pubchem. Pubchem. 1 July 2017.
2. Book: Richard P. Pohanish. Stanley A. Greene. Wiley Guide to Chemical Incompatibilities. 25 August 2009. John Wiley & Sons. 978-0-470-52330-8. 327–8.
3. Book: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 26: Ketones. 14 May 2014. Georg Thieme Verlag. 978-3-13-172011-5. 759–60.
4. 10.1104/pp.110.153601 . Detoxification without Intoxication: Herbicide Safeners Activate Plant Defense Gene Expression . 2010 . Riechers . Dean E. . Kreuz . Klaus . Zhang . Qin . Plant Physiology . 153 . 1 . 3–13 . 20237021 . 2862420 .