Chloromethyl methyl ether

Chloromethyl methyl ether[1]
Skeletal formula of chloromethyl methyl ether
Ball-and-stick model of the chloromethyl methyl ether molecule
Names
IUPAC name
Chloro(methoxy)methane
Other names
MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether
Identifiers
107-30-2 Yes
ChemSpider 13852893 
Jmol-3D images Image
KEGG C19160 
Properties
Molecular formula
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
MSDS http://www.cdc.gov/niosh/docs/81-123/pdfs/0129.pdf
Main hazards Carcinogen; Nocive; irritant
R-phrases R11 R20/21/22 R45
S-phrases S45 S53
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
3
3
2
Flash point 0 °C (32 °F; 273 K) (open cup)[2]
US health exposure limits (NIOSH):
OSHA-Regulated Carcinogen, no PEL[2]
Carcinogenic[2]
N.D.[2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
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]

References

  1. Sigma-Aldrich
  2. 2.0 2.1 2.2 2.3 2.4 "NIOSH Pocket Guide to Chemical Hazards #0129". National Institute for Occupational Safety and Health (NIOSH).
  3. Protective Groups in Organic Synthesis, T. W. Greene and P. G. M. Green, 3rd Edition, pages 27-33. ISBN 0-471-16019-9
  4. Synthesis of Alpha-Halo Ethers from Symmetric Acetals and In Situ Methoxymethylation of an Alcohol, Organic Syntheses, Vol. 84, No. 102 (2007)
  5. R.J. Linderman, M. Jaber, B.D. Griedel, J. Org. Chem. 1994, 59, 6499-6500.
  6. Monochloromethyl ether, Organic Syntheses I, 377
  7. bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
  8. "Chloromethyl methyl ether". U.S. Environmental Protection Agency, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.
  9. NIOSH Pocket Guide to Chemical Hazards
  10. Appendix B - Thirteen OSHA-Regulated Carcinogens