Chloromethyl methyl ether

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Chloromethyl methyl ether[1]
Chloromethyl methyl ether.svg
Identifiers
CAS number 107-30-2 YesY
ChemSpider 13852893 N
KEGG C19160 N
Jmol-3D images Image 1
Properties
Molecular formula C2H5ClO
Molar mass 80.51 g mol−1
Appearance Colorless liquid
Odor Irritant, 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)
Solubility in water Decompose
Solubility Soluble in alcohol and ether
Hazards
MSDS http://www.cdc.gov/niosh/docs/81-123/pdfs/0129.pdf
R-phrases R11 R20/21/22 R45
S-phrases S45 S53
Main hazards Carcinogen; Nocive; irritant
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
Flash point −17.8 °C (0.0 °F; 255.3 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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,[2] 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.[3] 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.[4] In contrast, the venerable procedure from formaldehyde, methanol and hydrogen chloride[5] yields material contaminated with a significant amount of the dangerous bis-chloromethyl ether and requires fractional distillation.

CMME is a known human carcinogen.[6] Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma.[7] It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit.[8][9]

References[edit]

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