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Chloromethyl methyl ether

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Chloromethyl methyl ether
Skeletal formula of chloromethyl methyl ether
Ball-and-stick model of the chloromethyl methyl ether molecule
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
EC Number
  • 203-480-1
KEGG
PubChem CID
RTECS number
  • KN6650000
UNII
UN number 1239
  • InChI=1S/C2H5ClO/c1-4-2-3/h2H2,1H3 ☒N
    Key: XJUZRXYOEPSWMB-UHFFFAOYSA-N ☒N
  • InChI=1/C2H5ClO/c1-4-2-3/h2H2,1H3
    Key: XJUZRXYOEPSWMB-UHFFFAOYAK
  • COCCl
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
Appearance Colorless 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)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Carcinogen & Irritant
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
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)
NIOSH (US health exposure limits):
PEL (Permissible)
OSHA-Regulated Carcinogen, no PEL
REL (Recommended)
Carcinogenic
IDLH (Immediate danger)
N.D.
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).
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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, 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.

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 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. 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.

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.

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

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


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