Chloroalkyl ether

Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH2)n-Cl, characterized as an ether connected to a chloromethyl group via an alkane chain.

Chloromethyl methyl ether (CMME) is an ether with the formula CH3OCH2Cl. It is used as an alkylating agent and industrial solvent to manufacture dodecylbenzyl chloride, water repellents, ion-exchange resins, polymers, and as a chloromethylation reagent. In organic synthesis the compound is used for the introduction of the methoxymethyl (MOM) protecting group.

Closely related compounds of industrial importance are bis(chloromethyl) ether (BCME) (closely related to chemical weapon sulfur mustard)[1] and benzyl chloromethyl ether (BOMCl).

Chloromethyl etherRMolar massCAS numberBoiling point °C
Benzyl chloromethyl etherBenzyl156.613587-60-8102 °C @ 14 mmHg (1.9 kPa)
Chloromethyl methyl etherMethyl80.51107-30-255-57
Bis(chloromethyl) ether114.96542-88-1106
tert-Butyl chloromethyl etherButyl124.5
2-Methoxyethoxymethyl chloride124.573970-21-650-52 °C @ 13 mmHg (1.7 kPa)
Dichloromethyl methyl ether114.964885-02-382 - 85.5 °C
Representative chloroalkyl ethers[2]

Methoxymethyl ethers (MOMs) and methoxyethyl ethers (MEMs) are common protecting groups in organic synthesis.

Safety

Chloroalkyl ethers are strong alkylating agents with attendant dangers. These compounds are human carcinogen.[3]

References
  1. Bis(Chloromethyl) ether Safety Data Sheet Archived 2009-01-13 at the Wayback Machine, Division of Occupational Health and Safety, US National Institutes of Health
  2. "Sigma-Aldrich: Analytical, Biology, Chemistry & Materials Science products and services".
  3. Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2, Report on carcinogens, Eleventh edition
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