(Chloromethyl) methyl ether

Structural formula
General
Surname	(Chloromethyl) methyl ether
other names	Chlorodimethyl ether; Monochlorodimethyl ether (MCD); Methoxymethyl chloride (MOMCl); Chloromethoxymethane;
Molecular formula	C 2 H 5 ClO
Brief description	colorless, highly flammable liquid
External identifiers / databases
EC number	203-480-1
ECHA InfoCard	100.003.165
PubChem	7864
Wikidata	Q158539
properties
Molar mass	80.51 g mol −1
Physical state	liquid
density	1.06 g cm −3
Melting point	−104 ° C
boiling point	59 ° C
Vapor pressure	213 mbar (20 ° C)
solubility	decomposition
Refractive index	1.396 (20 ° C)
safety instructions
H and P phrases	H: 225-302 + 312 + 332-319-350
	P: 201-210-280-305 + 351 + 338-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

(Chloromethyl) methyl ether is a chloroalkyl ether that is used for alkylation and for the production of water-repellent materials, ion exchange resins , polymers and as a chloromethylation reagent.

MOM protection group

(Chloromethyl) methyl ether is used for introduction of the methoxymethyl - protecting group (MOM) to alcohols is used. It is introduced with the help of a base that is consumed in the course of the reaction:

The resulting functional group is an acetal , which can be cleaved again by the action of acid, the original alcohol is formed back, and formaldehyde and methanol are also formed :

Carcinogenic effect

According to Appendix II, No. 6 of the German Ordinance on Hazardous Substances (GefStoffV), (chloromethyl) methyl ether is classified as a particularly dangerous carcinogenic substance and may only be manufactured or used in closed systems. The main route of exposure is through the respiratory tract. In carcinogenicity studies on rats, tissue changes were detected, particularly in the trachea and bronchi ( metaplasia and hyperplasia ). With regard to the carcinogenic potential, the results were inconsistent. It generally contains several percent of the symmetrical bis (chloromethyl) ether , whose carcinogenic effect on humans appears to be certain. Therefore, the following also applies to (chloromethyl) methyl ether: A carcinogenic effect in humans has been proven.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on (chloromethyl) methyl ether in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Data sheet Chloromethyl methyl ether, technical grade from Sigma-Aldrich , accessed on March 4, 2013 ( PDF ).
↑ Entry on chloromethyl methyl ether in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ PJ Kocienski: Protecting Groups . Georg Thieme Verlag, Stuttgart 2005, ISBN 3-13-135603-0 .
↑ Hazardous Substances Ordinance (GefStoffV) (as of April 2017).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on (chloromethyl) methyl ether in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[Sigma-2] Data sheet Chloromethyl methyl ether, technical grade from Sigma-Aldrich , accessed on March 4, 2013 ( PDF ).

[CLP_100.003.165-3] Entry on chloromethyl methyl ether in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Protecting_Groups-4] PJ Kocienski: Protecting Groups . Georg Thieme Verlag, Stuttgart 2005, ISBN 3-13-135603-0 .

[5] Hazardous Substances Ordinance (GefStoffV) (as of April 2017).