Dichloroacetyl chloride

Dichloroacetyl chloride

Names
Preferred IUPAC name 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, 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.

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   978-3-527-30673-2.
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.