Chloroalkyl ether explained

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 . 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 etherRChemical structureMolar mass
(g/mol)
CAS numberBoiling point
(°C)
Benzyl chloromethyl etherBenzyl156.613587-60-8102 °C @ 14mmHg
Chloromethyl methyl etherMethyl80.51107-30-255-57
Bis(chloromethyl) etherChloromethyl114.96542-88-1106
tert-Butyl chloromethyl ethertert-Butyl124.540556-01-2
2-Methoxyethoxymethyl chlorideMethoxyethyl124.573970-21-650-52 °C @ 13mmHg
Dichloromethyl methyl etherMethyl114.964885-02-382 - 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]

Notes and References

  1. http://dohs.ors.od.nih.gov/pdf/Bis_chloromethyl_%20ether%20REVISED.pdf Bis(Chloromethyl) ether Safety Data Sheet
  2. Web site: Sigma-Aldrich: Analytical, Biology, Chemistry & Materials Science products and services.
  3. https://ntp.niehs.nih.gov/ntp/roc/content/profiles/bis_chloromethyletherandtechnical-gradechloromethylmethylether.pdf Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2