Chloromethyl methyl ether (CMME) is an ether with the formula Template:MethylOCH2Template:Chlorine. It is used as an alkylating agent and industrial solvent to manufacture dodecylbenzyl chloride, water repellents, ion-exchange resins, polymers, and as a chloromethylation reagent. It is a known human carcinogen . In organic synthesis the compound is used for the introduction of the methoxymethyl(MOM) protecting group.
|Chloromethyl ether||R||Molar mass||CAS number||Boiling point °C|
|benzyl chloromethyl ether||Benzyl||benzyl chloromethyl ether||121.93||98-80-6||102 14 mm Hg|
|methyl chloromethyl ether||Methyl||methyl chloromethyl ether||80.51||107-30-2||55-57|
|bischloromethyl ether||File:Bis(chloromethyl ether)2.svg||114.96||542-88-1||106|
|Representative chloroalkyl ethers |
The MOM group can be removed by application of dilute acid.
An example is the protection of a phenol group :
With a benzyl group the protective group becomes a BOM-ether. See also the closely related methylthiomethyl ethers.
- bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
- Bis(Chloromethyl) ether Safety Data Sheet Division of Occupational Health and Safety US National Institutes of Health LInk
- Enantioselective total synthesis of (2)-heliannuol A Hidetoshi Kishuku, Mitsuru Shindo and Kozo Shishido Chem. Commun., 2003, 350–351 Article link