Chloromethyl methyl ether (CMME) is a

compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...

with formula CH₃OCH₂Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...

. In organic synthesis, it is used for introducing the

methoxymethyl ether In organic chemistry, a methoxymethyl ether is a functional group with the formula , abbreviated MOM. Methoxymethyl ethers are often employed in organic synthesis to protect alcohols. They are usually derived from 2-methoxymethyl chloride. Clos ...

(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 The Blanc chloromethylation (also called the Blanc reaction) is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride to form chloromethyl arenes. The reaction is catalyzed by Lewis acids such as zinc chloride. The rea ...

Preparation

A convenient synthesis of chloromethyl methyl ether ''in situ'' involves the reaction of

dimethoxymethane Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimeth ...

and acetyl chloride in the presence of a Lewis acid catalyst This route affords a

methyl acetate Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish remo ...

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 ''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and ex ...

'' employing

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...

, methanol, and

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

yields material significantly contaminated with the dangerous

bis(chloromethyl) ether 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 ...

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 A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

. Chronic exposure can increase the incidence of

respiratory The respiratory system (also respiratory apparatus, ventilatory system) is a biological system consisting of specific organs and structures used for gas exchange in animals and plants. The anatomy and physiology that make this happen varies gre ...

cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...

s, including

small cell carcinoma Small-cell carcinoma is a type of highly malignant cancer that most commonly arises within the lung, although it can occasionally arise in other body sites, such as the cervix, prostate, and gastrointestinal tract. Compared to non-small cell c ...

.Chloromethyl methyl ether
.

U.S. Environmental Protection Agency The Environmental Protection Agency (EPA) is an Independent agencies of the United States government, independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon pro ...

, Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011. It is one of 13 chemicals regulated by the

Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agenc ...

despite not having an established

permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational ...

.NIOSH Pocket Guide to Chemical Hazards
/ref>
/ref> 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 The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness. On October ...

(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.http://laws-lois.justice.gc.ca/PDF/SOR-2012-285.pdf {{Bare URL PDF, date=March 2022

References

Reagents for organic chemistry Alkylating agents Protecting groups Organochlorides Ethers IARC Group 1 carcinogens