2146. Chloromethyl Methyl Ether

Nomenclature

CAS number: 107-30-2
Chloromethoxymethane; methyl chloromethyl ether; monochloromethyl ether; chlorodimethyl ether; CMME.
C2H5ClO; mol wt 80.51.
C 29.84%, H 6.26%, Cl 44.04%, O 19.87%.

Description and references

Prepd by passing HCl through a mixture of formalin and methanol: C. S. Marvel, P. K. Porter, Org. Synth. coll. vol. I, 377 (1941). See also Beilstein 1, 580 (1918) and supplements. Commercial product usually contaminated by sym-dichloromethyl ether, q.v. Review of carcinogenic risk: IARC Monographs 4, 239-245 (1974).

Chemical structure

Properties

Colorless liquid, bp 59°. d420 1.0605. nD20 1.39737.

Caution

Potential symptoms of overexposure are irritation of eyes, skin and mucous membranes; pulmonary edema, pulmonary congestion and pneumonia; skin burns, necrosis; coughing, wheezing; blood stained sputum; weight loss; bronchial secretions. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 66. The technical grade is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-56.

Use

In synthesis of chloromethylated compounds, plastics and ion-exchange resins.