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Chloromethyl methyl ether^[1]
Names
	Preferred IUPAC name Chloro(methoxy)methane
	Other names MOM-Cl, CMME, MCD, Chlorodimethyl ether, Chloromethoxymethane, Dimethylchloroether, Methylchloromethyl ether
Identifiers
CAS Number	107-30-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	13852893 ;
ECHA InfoCard	100.003.165
EC Number	203-480-1;
KEGG	C19160 ;
PubChem CID	7864;
RTECS number	KN6650000;
UNII	334G5B96VG ;
UN number	1239
CompTox Dashboard (EPA)	DTXSID6020307 ;
	InChI InChI=1S/C2H5ClO/c1-4-2-3/h2H2,1H3 Key: XJUZRXYOEPSWMB-UHFFFAOYSA-N ; InChI=1/C2H5ClO/c1-4-2-3/h2H2,1H3 Key: XJUZRXYOEPSWMB-UHFFFAOYAK;
	SMILES COCCl;
Properties
Chemical formula	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)
Solubility in water	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H319, H332, H350
Precautionary statements	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). verify (what is ?) Infobox references

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]

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]