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{{chembox| Verifiedfields = changed| Watchedfields = changed| verifiedrevid = 329011034| ImageFile = Chloromethyl methyl ether.svg| ImageSize = 140px| ImageAlt = Skeletal formula of chloromethyl methyl ether| ImageFile1 = Chloromethyl methyl ether 3D ball.png| ImageSize1 = 150| ImageAlt1 = Ball-and-stick model of the chloromethyl methyl ether molecule

Sigma-Aldrich| PIN = Chloro(methoxy)methane| OtherNames = MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether|Section1={{Chembox Identifiers

correct|CAS}}| CASNo = 107-30-2

changed|FDA}}| UNII = 334G5B96VG

changed|kegg}}| KEGG = C19160

changed|chemspider}}| ChemSpiderID = 13852893| PubChem = 7864| EC_number = 203-480-1| RTECS = KN6650000| UNNumber = 1239| SMILES = COCCl| InChI = 1/C2H5ClO/c1-4-2-3/h2H2,1H3| InChIKey = XJUZRXYOEPSWMB-UHFFFAOYAK

changed|chemspider}}| StdInChI = 1S/C2H5ClO/c1-4-2-3/h2H2,1H3

changed|chemspider}}| StdInChIKey = XJUZRXYOEPSWMB-UHFFFAOYSA-N }}|Section2={{Chembox Properties

H=5

O=1| Appearance = Colorless liquid| Odor = Irritating and acrid| MeltingPtC = −103.5 | BoilingPtC = 55-57 | Density=1.06 g/mL | Solubility = reacts| SolubleOther = Soluble in alcohol and diethylether| VaporPressure = 192 mmHg (21°C) }}|Section3={{Chembox Hazards| MainHazards = Carcinogen & Irritant| ExternalSDS = Safety Data Sheet westliberty.edu/health-and-safety/files/2010/02/Chloromethyl-methyl-ether.pdf" title="web.archive.org/web/20170914222545westliberty.edu/health-and-safety/files/2010/02/Chloromethyl-methyl-ether.pdf">Archived| GHSSignalWord = Danger| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}

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405|501}}| FlashPtC = 0| FlashPt_notes = (open cup)| NFPA-H = 3| NFPA-F = 3| NFPA-R = 2

0129}}| PEL = OSHA-Regulated Carcinogen, no PEL| REL = Carcinogenic }} }}Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (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. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.BOOK, 10.1002/047084289X.rc118, Chloromethyl Methyl Ether, Encyclopedia of Reagents for Organic Synthesis, 2001, Wuts, Peter G. M., 0471936235, Preparation A convenient synthesis of chloromethyl methyl ether in situ involves the reaction of dimethoxymethane and acetyl chloride in the presence of a Lewis acid catalystJOURNAL, Berliner, Martin A., Belecki, Katherine, Synthesis of alpha-Halo Ethers from Symmetric Acetals and in situ Methoxymethylation of an Alcohol, Organic Syntheses, 2007, 84, 102, 10.15227/orgsyn.084.0102, free, This route affords a methyl acetate solution of chloromethyl methyl ether of high purity. A similar method, using a high-boiling acyl chloride, can be used to prepare pure, dimethoxymethane being the only contaminant.R.J. Linderman, M. Jaber, B.D. Griedel, J. Org. Chem. 1994, 59, 6499-6500. In contrast, the classical procedure reported in Organic Syntheses employing formaldehyde, methanol, and hydrogen chloride yields material significantly contaminated with the dangerous bis(chloromethyl) ether and requires fractional distillation.JOURNAL, Monochloromethyl Ether, Organic Syntheses, C. S. Marvel and P. K. Porter, 1929, 9, 58, 10.15227/orgsyn.009.0058, Safety The amount of time required to destroy residual chloromethyl methyl ether using various standard aqueous quench solutions (ammonium chloride solution, water, and sodium carbonate solution) has been measured. In all cases, a solution of chloromethyl methyl ether in toluene/methyl acetate was destroyed (to within detection limit) after vigorous stirring with the quench solution for 15 minutes.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 HazardsAppendix B - Thirteen OSHA-Regulated CarcinogensIt 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.JOURNAL, United States Government Publishing Office, Government Printing Office, 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities,edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf, July 1, 2008, October 29, 2011,edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf," title="web.archive.org/web/20120225051612edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf,">web.archive.org/web/20120225051612edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf, February 25, 2012, dead, It listed in Schedule 1 Part 1 of Canada’s Prohibition of Certain Toxic Substances Regulationslaws-lois.justice.gc.ca/PDF/SOR-2012-285.pdf {{Bare URL PDF|date=March 2022}} References