Chloromethyl methyl ether
MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether
3D model (JSmol)
|Molar mass||80.51 g·mol−1|
|Odor||Irritating, 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||Soluble in alcohol and ether|
|Vapor pressure||192 mmHg (21°C)|
|Main hazards||Carcinogen; Nocive; irritant|
|Safety data sheet||https://www.cdc.gov/niosh/docs/81-123/pdfs/0129.pdf|
|GHS signal word||Danger|
|H225, H302, H312, H319, H332, H350|
|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281|
|Flash point||0 °C (32 °F; 273 K) (open cup)|
|US health exposure limits (NIOSH):|
|OSHA-Regulated Carcinogen, no PEL|
IDLH (Immediate danger)
Except where otherwise noted, 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.
It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. It listed in Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations.
- "NIOSH Pocket Guide to Chemical Hazards #0129". National Institute for Occupational Safety and Health (NIOSH).
- 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
- "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011.