Chloromethyl methyl ether

Last updated
Chloromethyl methyl ether [1]
Chloromethyl methyl ether.svg
Chloromethyl methyl ether 3D ball.png
Names
Preferred 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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-480-1
KEGG
PubChem CID
RTECS number
  • KN6650000
UNII
UN number 1239
  • InChI=1S/C2H5ClO/c1-4-2-3/h2H2,1H3 X mark.svgN
    Key: XJUZRXYOEPSWMB-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C2H5ClO/c1-4-2-3/h2H2,1H3
    Key: XJUZRXYOEPSWMB-UHFFFAOYAK
  • COCCl
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
AppearanceColorless liquid
Odor Irritating and acrid
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)
reacts
Solubility Soluble in alcohol and diethylether
Vapor pressure 192 mmHg (21°C) [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Carcinogen & Irritant
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H302, H312, H319, H332, H350
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P322, P330, P337+P313, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
3
3
2
Flash point 0 °C (32 °F; 273 K) (open cup) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
OSHA-Regulated Carcinogen, no PEL [2]
REL (Recommended)
Carcinogenic [2]
IDLH (Immediate danger)
N.D. [2]
Safety data sheet (SDS) Safety Data Sheet Archived
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group, [3] and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation. [4]

Contents

Preparation

A convenient synthesis of chloromethyl methyl ether in situ involves the reaction of dimethoxymethane and acetyl chloride in the presence of a Lewis acid catalyst [5] This route affords a methyl acetate solution of chloromethyl methyl ether of high purity. A similar method, using a high-boiling acyl chloride, can be used to prepare pure, dimethoxymethane being the only contaminant. [6] In contrast, the classical procedure reported in Organic Syntheses employing formaldehyde, methanol, and hydrogen chloride yields material significantly contaminated with the dangerous bis(chloromethyl) ether and requires fractional distillation. [7]

Safety

The amount of time required to destroy residual chloromethyl methyl ether using various standard aqueous quench solutions (ammonium chloride solution, water, and sodium carbonate solution) has been measured. In all cases, a solution of chloromethyl methyl ether in toluene/methyl acetate was destroyed (to within detection limit) after vigorous stirring with the quench solution for 15 minutes. [5]

CMME is a known human carcinogen. [8] Chronic exposure can increase the incidence of respiratory cancers, including small cell carcinoma. [9] It is one of 13 chemicals regulated by the Occupational Safety and Health Administration despite not having an established permissible exposure limit. [10] [11]

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. [12] It listed in Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations. [13]

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<span class="mw-page-title-main">Bis(chloromethyl) ether</span> Chemical compound

Bis(chloromethyl) ether is an organic compound with the chemical formula (CH2Cl)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale, but was found to be highly carcinogenic and thus such production has ceased.

In organic chemistry, a methoxymethyl ether is a functional group with the formula ROCH2OCH3, abbreviated MOM. Methoxymethyl ethers are often employed in organic synthesis to protect alcohols. They are usually derived from 2-methoxymethyl chloride. Closely related to MOM ethers are methoxyethoxymethoxy (MEM) protecting groups, introduced using 2-methoxyethoxymethyl chloride. The MEM protecting groups are more easily installed and more easily removed.

Bis(chloroethyl) ether is an organic compound with the formula O(CH2CH2Cl)2. It is an ether with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a chlorinated solvent.

<span class="mw-page-title-main">Dichloroacetylene</span> Chemical compound

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References

  1. ↑ Sigma-Aldrich
  2. 1 2 3 4 5 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. ↑ Wuts, Peter G. M. (2001). "Chloromethyl Methyl Ether". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc118. ISBN   0471936235.
  5. 1 2 Berliner, Martin A.; Belecki, Katherine (2007). "Synthesis of alpha-Halo Ethers from Symmetric Acetals and in situ Methoxymethylation of an Alcohol". Organic Syntheses. 84: 102. doi:10.15227/orgsyn.084.0102.
  6. ↑ R.J. Linderman, M. Jaber, B.D. Griedel, J. Org. Chem.1994,59, 6499-6500.
  7. ↑ C. S. Marvel and P. K. Porter (1929). "Monochloromethyl Ether". Organic Syntheses. 9: 58. doi:10.15227/orgsyn.009.0058.
  8. ↑ bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
  9. ↑ "Chloromethyl methyl ether". U.S. Environmental Protection Agency, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.
  10. ↑ NIOSH Pocket Guide to Chemical Hazards
  11. ↑ Appendix B - Thirteen OSHA-Regulated Carcinogens
  12. ↑ "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. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.{{cite journal}}: Cite journal requires |journal= (help)
  13. ↑ http://laws-lois.justice.gc.ca/PDF/SOR-2012-285.pdf [ bare URL PDF ]
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