View source for Chloroalkyl ether



==Overview==
[[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>''bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2'' [http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s039bcme.pdf 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>''Bis(Chloromethyl) ether Safety Data Sheet'' Division of Occupational Health and Safety
US National Institutes of Health [http://dohs.ors.od.nih.gov/pdf/Bis_chloromethyl_%20ether%20REVISED.pdf LInk]</ref> and '''benzyl chloromethyl ether'''.


{|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||98-80-6||102 14 mm Hg
|-
|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
|-
| 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]] 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.

==References==
{{Reflist}}



[[Category:Ethers]]


[[ja:クロロメチルメチルエーテル]]
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