Dichloroacetyl chloride

Dichloroacetyl chloride
Identifiers
CAS Number	79-36-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	1209426
ChEBI	CHEBI:34688;
ChEMBL	ChEMBL449486;
ChemSpider	21106100;
ECHA InfoCard	100.001.091
EC Number	201-199-9;
Gmelin Reference	430743
KEGG	C14867;
PubChem CID	6593;
RTECS number	AO6650000;
UNII	52O60099FY;
UN number	1765
CompTox Dashboard (EPA)	DTXSID6024965 ;
	InChI InChI=1S/C2HCl3O/c3-1(4)2(5)6/h1H Key: FBCCMZVIWNDFMO-UHFFFAOYSA-N;
	SMILES C(C(=O)Cl)(Cl)Cl;
Properties
Chemical formula	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).
	Infobox references

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, 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

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.

References

"Pubchem". Pubchem. Retrieved 1 July 2017.
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.
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.
Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537.

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[Pubchem-1] "Pubchem". Pubchem. Retrieved 1 July 2017.

[PohanishGreene2009-2] 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.

[Ullmann-4] Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537.