2067. Chloracetyl Chloride

Nomenclature

CAS number: 79-04-9
C2H2Cl2O; mol wt 112.94.
C 21.27%, H 1.78%, Cl 62.78%, O 14.17%.
ClCH2COCl.

Description and references

Prepn from chloroacetic acid and benzoyl chloride: Brown, J. Am. Chem. Soc. 60, 1325 (1938); by chlorination of ketene: Erickson, Prill, J. Org. Chem. 23, 141 (1958); Prill, US 2889365 (1959 to Monsanto); from chloroacetic acid and pyrocatechylphosphorus trichloride: Gross, Gloede, Ber. 96, 1387 (1963). Manuf from chloroacetic acid and POCl2: MacKenzie, Morris, US 2848491 (1958 to Dow); from ketene: Prill, US 2889365 (1959 to Monsanto). Physical data: McDonald et al., J. Chem. Eng. Data 4, 311 (1959).

Properties

Liquid, very pungent odor. bp 106°. mp -21.77°. d420 1.4202. nD20 1.4541. Dec by water. Protect from moisture.

Caution

Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; eye and skin burns; cough, wheezing, dyspnea, lacrimation. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 60.

Use

In the synthesis of organic compounds.