View source for Chloroalkyl ether

[[Image:CMME.png|right|thumb|200px|Chemical structure of chloromethyl methyl ether.]]
'''Chloroalkyl ethers''' are a class of [[organic compound]]s with the general structure R-O-(CH<sub>2</sub>)<sub>n</sub>-Cl, characterized as an [[ether]] connected to a [[organohalide|chloromethyl]] group via a [[alkane]] chain. 

[[Chloromethyl methyl ether]] (CMME) is an [[ether]] with the formula {{methyl}}{{oxygen}}{{carbon}}{{hydrogen|2}}{{chlorine}}. It is used as an [[alkylating agent]] and industrial [[solvent]] to manufacture [[dodecylbenzyl chloride]], [[water repellent]]s, [[ion-exchange resin]]s, [[polymer]]s, and as a chloromethylation [[reagent]]. It is a known human [[carcinogen]].<ref>[http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s039bcme.pdf Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2], ''Report on carcinogens'', Eleventh edition</ref> 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]])<ref>[http://dohs.ors.od.nih.gov/pdf/Bis_chloromethyl_%20ether%20REVISED.pdf Bis(Chloromethyl) ether Safety Data Sheet], Division of Occupational Health and Safety, US National Institutes of Health</ref> and '''benzyl chloromethyl ether''' (BOMCl).


{|align="center"  class="wikitable"
|Chloromethyl ether|||R|||||[[Molar mass]]||[[CAS number]]||[[Boiling point]] °C
|-
|Benzyl chloromethyl ether||[[Benzyl]]||[[Image:Benzyl chloromethyl ether2.svg|100px|benzyl chloromethyl ether]]||121.93||3587-60-8||102°C @ {{convert|14|mmHg|abbr=on}}
|-
|Methyl chloromethyl ether||[[Methyl]]||[[Image:Methyl chloromethyl ether2.svg|100px|methyl chloromethyl ether]]||80.51||107-30-2||55-57
|-
|Bischloromethyl ether||||[[Image:Bis(chloromethyl ether)2.svg|100px|]]||114.96||542-88-1||106
|-
|''t''-Butoxymethyl ether||[[Butyl]]||[[Image:T-Butoxymethyl chloride.svg|100px|]]||124.5||||
|-
|Methoxyethoxymethyl ether||||[[Image:Methoxyethoxymethyl chloride.svg|100px|]]||124.57||3970-21-6||50-52°C @ {{convert|13|mmHg|abbr=on}}
|-
|[[Dichloromethyl methyl ether]]||||[[File:Dichloromethyl methyl ether.svg|100px|]]||114.96||4885-02-3||82 - 85.5°C 
|-
| colspan=6 align=left style="background: #ccccff;"| '''Representative chloroalkyl ethers''' <ref>www.sigmaaldrich.com</ref>
|}

==MOM ethers==
Methyl chloromethyl ether (often abbreviated '''MOMCl''') is used as a [[protecting group]] for [[alcohol]]s. The product formed is a '''MOM ether'''. A base such as [[N,N-Diisopropylethylamine|''N'',''N''-diisopropylethylamine]] is a requirement. 

:[[image:Methoxymethylation.svg|350px|methoxymethylation]]

The MOM group can be removed by application of dilute acid. 

:[[image:Demethoxymethylation.svg|350px|demethoxymethylation]]

An example is the protection of a phenol group:<ref>''Enantioselective total synthesis of (2)-heliannuol'' A Hidetoshi Kishuku, Mitsuru Shindo and Kozo Shishido [[Chem. Commun.]], '''2003''', 350–351 [http://rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b211227b&JournalCode=CC Article link]</ref>

:[[Image:MOMprotectinggroup2.svg|Example of MOM ether protection]]

With a benzyl group the protective group becomes a '''BOM-ether'''. See also the closely related [[methylthiomethyl ether]]s.

With a ''t''-butyl group the protective group becomes a '''Bum-ether'''.  The chloride is prepaired from [[Methyl tert-butyl ether]] using a photochemical chlorination.<ref>[http://folk.uio.no/toreben/a-monohalo-ethers/Reactions/Reactions/Protection%20chemistry/Protection.html Protection chemistry] Professor Tore Benneche, University of Oslo</ref>

With a methoxyethoxyl group the protective group becomes a '''MEM-ether'''.  This ether is much more stable than the MOM ether to hydrolysis.

==References==
{{Reflist}}

[[Category:Ethers]]
[[Category:Organochlorides]]

[[es:Éter de cloroalquilo]]
[[fr:Chlorométhyl-méthyl-éther]]
[[ja:クロロメチルメチルエーテル]]
[[Category:2Fix]]