Chloromethyl methyl ether (CMME) is an ether with the formula CH3OCH2Cl. 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||156.61||3587-60-8||102°C @ 14 mmHg (1.9 kPa)|
|Chloromethyl methyl ether||Methyl||80.51||107-30-2||55-57|
|tert-Butyl chloromethyl ether||Butyl||124.5|
|Methoxyethyl chloromethyl ether||124.57||3970-21-6||50-52°C @ 13 mmHg (1.7 kPa)|
|Dichloromethyl methyl ether||114.96||4885-02-3||82 - 85.5°C|
|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.
With a methoxyethoxyl group the protective group becomes a MEM-ether. This ether is much more stable than the MOM ether to hydrolysis.
- 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
- Enantioselective total synthesis of (2)-heliannuol A Hidetoshi Kishuku, Mitsuru Shindo and Kozo Shishido Chem. Commun., 2003, 350–351 Article link
- Protection chemistry Professor Tore Benneche, University of Oslo