In organic synthesis, it is used for introducing the methoxyethoxy ether (MEM) protecting group.
[2] MEM protecting groups are generally preferred to methoxymethyl (MOM) protecting groups, both in terms of formation and removal.
Typically, the alcohol to be protected is deprotonated with a non-nucleophilic base such as N,N-diisopropylethylamine (DIPEA, Hunig's base) in dichloromethane followed by addition of 2-methoxyethoxymethyl chloride.
[3] [4] The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.
[5] The closely related chloromethyl methyl ether is a known human carcinogen.