chloroalkyl ether

File:(Chlormethyl)methylether.svg

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 {{chem2|auto=1|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)[http://dohs.ors.od.nih.gov/pdf/Bis_chloromethyl_%20ether%20REVISED.pdf Bis(Chloromethyl) ether Safety Data Sheet] {{Webarchive|url=https://web.archive.org/web/20090113175638/http://dohs.ors.od.nih.gov/pdf/Bis_chloromethyl_%20ether%20REVISED.pdf |date=2009-01-13 }}, Division of Occupational Health and Safety, US National Institutes of Health and benzyl chloromethyl ether (BOMCl).

align="center" class="wikitable" |Chloromethyl ether	|R	Chemical structure	|Molar mass (g/mol)	CAS number	Boiling point (°C)
Benzyl chloromethyl ether	Benzyl	File:Benzyl chloromethyl ether.svg	156.61	3587-60-8	102 °C @ {{convert|14|mmHg|abbr=on}}
Chloromethyl methyl ether	Methyl	File:(Chlormethyl)methylether.svg	80.51	107-30-2	55-57
Bis(chloromethyl) ether	Chloromethyl	100px	114.96	542-88-1	106
tert-Butyl chloromethyl ether	tert-Butyl	100px	124.5	40556-01-2
2-Methoxyethoxymethyl chloride	Methoxyethyl	100px	124.57	3970-21-6	50-52 °C @ {{convert|13|mmHg|abbr=on}}
Dichloromethyl methyl ether	Methyl	100px	114.96	4885-02-3	82 - 85.5 °C
colspan=6 align=left style="background: #ccccff;"| Representative chloroalkyl ethers{{Cite web | url=http://www.sigmaaldrich.com | title=Sigma-Aldrich: Analytical, Biology, Chemistry & Materials Science products and services}}

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