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|Section2= |Section3= }} 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,〔''Protective Groups in Organic Synthesis'', T. W. Greene and P. G. M. Green, 3rd Edition, pages 27-33. ISBN 0-471-16019-9〕 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.〔''Synthesis of Alpha-Halo Ethers from Symmetric Acetals and In Situ Methoxymethylation of an Alcohol'', Organic Syntheses, Vol. 84, No. 102 (2007)〕 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.〔R.J. Linderman, M. Jaber, B.D. Griedel, ''J. Org. Chem.'' 1994, ''59,'' 6499-6500.〕 In contrast, the venerable procedure from formaldehyde, methanol and hydrogen chloride〔''Monochloromethyl ether'', Organic Syntheses ''I'', 377〕 yields material contaminated with a significant amount of the dangerous ''bis''-chloromethyl ether and requires fractional distillation. CMME is a known human carcinogen.〔''bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2'' (Report on carcinogens, eleventh edition )〕 Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma.〔"(Chloromethyl methyl ether )". U.S. Environmental Protection Agency, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.〕 It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit.〔(NIOSH Pocket Guide to Chemical Hazards )〕〔(Appendix B - Thirteen OSHA-Regulated Carcinogens )〕 ==References== 〔 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Chloromethyl methyl ether」の詳細全文を読む スポンサード リンク
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