Chloromethyl methyl ether
|Chloromethyl methyl ether|
|Jmol-3D images||Image 1|
|Molar mass||80.51 g mol−1|
|Odor||Irritant, HCl like|
|Melting point||−103.5 °C (−154.3 °F; 169.7 K)|
|Boiling point||55–57 °C (131–135 °F; 328–330 K)|
|Solubility in water||Decompose|
|Solubility||Soluble in alcohol and ether|
|R-phrases||R11 R20/21/22 R45|
|Main hazards||Carcinogen; Nocive; irritant|
|Flash point||−17.8 °C (0.0 °F; 255.3 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. It is a chloroalkyl ether. 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. In organic synthesis, it is used for introducing the methoxymethyl (MOM) protecting group, and is thus often called MOM-Cl or MOM chloride.
A convenient method to prepare MOM chloride in situ is by using dimethoxymethane and an acyl chloride in the presence of catalytic Lewis acid. A very similar method, using a high-boiling acyl chloride, can be used to prepare pure material. This method yields > 93 % pure material with dimethoxymethane as the only contaminant. In contrast, the venerable procedure from formaldehyde, methanol and hydrogen chloride yields material contaminated with a significant amount of the dangerous bis-chloromethyl ether and requires fractional distillation.
CMME is a known human carcinogen. Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma. It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit.
- Protective Groups in Organic Synthesis, T. W. Greene and P. G. M. Green, 3rd Edition, pages 27-33. ISBN 0-471-16019-9
- Synthesis of Alpha-Halo Ethers from Symmetric Acetals and In Situ Methoxymethylation of an Alcohol, Organic Syntheses, Vol. 84, No. 102 (2007)
- R.J. Linderman, M. Jaber, B.D. Griedel, J. Org. Chem. 1994, 59, 6499-6500.
- Monochloromethyl ether, Organic Syntheses I, 377
- bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
- "Chloromethyl methyl ether". U.S. Environmental Protection Agency, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.
- NIOSH Pocket Guide to Chemical Hazards