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