Chloromethyl methyl ether
Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl; it is a chloroalkyl ether.
- CAS No.
- 107-30-2
- Molecular formula
- C2H5ClO
- Molecular weight
- 80.51 g/mol
- Purity
- On request
AppearanceColourless to pale yellow liquid
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Overview
It is used as an alkylating agent and industrial solvent in the manufacture of dodecylbenzyl chloride, water repellents, ion exchange resins and polymers. In organic synthesis it is used to introduce the methoxymethyl (MOM) protecting group and as a chloromethylation agent in some versions of the Blanc chloromethylation.
It can be generated in situ from dimethoxymethane and acetyl chloride as a solution in methyl acetate of >95% purity; the classical Organic Syntheses route (formaldehyde, methanol, HCl) gives material contaminated with bis(chloromethyl) ether requiring fractional distillation. Residual CMME was destroyed within detection limits after 15 minutes of vigorous stirring with aqueous ammonium chloride, water or sodium carbonate.
CMME is a known human carcinogen; chronic exposure is linked to respiratory cancers including small-cell carcinoma. It is one of 13 chemicals regulated by OSHA, an extremely hazardous substance under US EPCRA Section 302, and listed in Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations.
Applications
- Alkylating agent
- Industrial solvent in making dodecyl benzyl chloride detergent, water repellents and ion exchange resins
- Introducing the methoxymethyl (MOM) protecting group
- Chloromethylation agent (Blanc chloromethylation)
Technical specifications
| RTECS number | KN6650000 |
|---|---|
| Boiling point | 55-59ºC |
| Flash Point | 15ºC |
| Density | 1.06 |
| Vapor Pressure | 3.55 psi (20 °C) |
| Water Solubility | decomposes |
Packaging & storage
0-6ºC
Safety information
- Known human carcinogen; regulated by OSHA; extremely hazardous substance under US Section 302; Schedule 1 Part 1 of Canada's Prohibition of Certain Toxic Substances Regulations.
Full details are in the Safety Data Sheet, sent with every quotation.