Chloromethyl methyl ether
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| Names | |
|---|---|
| IUPAC name
Chloro(methoxy)methane | |
| Other names
MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether | |
| Identifiers | |
107-30-2  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 13852893  |
| ECHA InfoCard | 100.003.165 |
| KEGG | C19160 |
| UNII | 334G5B96VG |
| |
| |
| Properties | |
| C2H5ClO | |
| Molar mass | 80.51 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Irritating, HCl like |
| Density | 1.06 g/mL |
| Melting point | −103.5 °C (−154.3 °F; 169.7 K) |
| Boiling point | 55–57 °C (131–135 °F; 328–330 K) |
| Decompose | |
| Solubility | Soluble in alcohol and ether |
| Vapor pressure | 192 mmHg (21°C)[2] |
| Hazards | |
| Main hazards | Carcinogen; Nocive; irritant |
| Safety data sheet | http://www.cdc.gov/niosh/docs/81-123/pdfs/0129.pdf |
| R-phrases | R11 R20/21/22 R45 |
| S-phrases | S45 S53 |
| NFPA 704 | |
| Flash point | 0 °C (32 °F; 273 K) (open cup)[2] |
| US health exposure limits (NIOSH): | |
| PEL (Permissible) |
OSHA-Regulated Carcinogen, no PEL[2] |
| REL (Recommended) |
Carcinogenic[2] |
| IDLH (Immediate danger) |
N.D.[2] |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
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,[3] 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.[4] 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.[5] In contrast, the venerable procedure from formaldehyde, methanol and hydrogen chloride[6] yields material contaminated with a significant amount of the dangerous bis-chloromethyl ether and requires fractional distillation.
CMME is a known human carcinogen.[7] Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma.[8] It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit.[9][10]
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.[11]
References
- ↑ Sigma-Aldrich
- 1 2 3 4 5 "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.