Chloromethyl methyl ether

From Wikipedia, the free encyclopedia
Jump to: navigation, search
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.165
EC Number 203-480-1
KEGG
RTECS number KN6650000
UNII
UN number 1239
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 https://www.cdc.gov/niosh/docs/81-123/pdfs/0129.pdf
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H225, H302, H312, H319, H332, H350
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281
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 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).
N verify (what is YesYN ?)
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] It listed in Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations.[12]

References[edit]

  1. ^ Sigma-Aldrich
  2. ^ a b c d e "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
  11. ^ "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. 
  12. ^ http://laws-lois.justice.gc.ca/PDF/SOR-2012-285.pdf