2-Methoxyethoxymethyl chloride

Methoxyethoxymethyl chloride.svg 1-(Chloromethoxy)-2-methoxyethane 3970-21-6 69995 223-589-8 A5RRM67QUG 77590 1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3 BIAAQBNMRITRDV-UHFFFAOYSA-N COCCOCCl 4 9 1 2 colorless liquid 1.094 g cm−3 50-52 13 mm Hg 2-Methoxyethoxymethyl chloride https://pubchem.ncbi.nlm.nih.gov/compound/77590#section=Safety-and-Hazards https://web.archive.org/web/20220325132757/https://pubchem.ncbi.nlm.nih.gov/compound/77590#section=Safety-and-Hazards dead March 25, 2022 pubchem.ncbi.nlm.nih.gov en 02 07 08 Danger 226 302 315 319 335 203 210 233 240 241 242 243 261 264 264+265 270 271 280 301+317 302+352 303+361+353 304+340 305+351+338 318 319 321 330 332+317 337+317 362+364 370+378 403+233 403+235 405 501 2-Methoxyethoxymethyl chloride is an organic compound with formula CH3OCH2CH2OCH2Cl. A colorless liquid, it is classified as a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxyethoxy ether (MEM) protecting group.10.1002/047084289X.rm100 2-Methoxyethoxymethyl Chloride Encyclopedia of Reagents for Organic Synthesis 2001 Wuts Peter G. M. 0471936235 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. Corey E. J. Gras Jean-Louis Ulrich Peter 1976-03-01 A new general method for protection of the hydroxyl function Tetrahedron Letters 17 11 809–812 10.1016/S0040-4039(00)92890-9 Lee Hong Myung Nieto-Oberhuber Cristina Shair Matthew D. 2008-12-17 Enantioselective Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation Journal of the American Chemical Society 130 50 16864–16866 10.1021/ja8071918 0002-7863 19053422 2008JAChS.13016864L 207132632 none|thumb|626x626px The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.Amano Seiji Takemura Noriaki Ohtsuka Masami Ogawa Seiichiro Chida Noritaka 1999-03-26 Total synthesis of paniculide A from d-glucose Tetrahedron 55 13 3855–3870 10.1016/S0040-4020(99)00096-4 Safety The closely related chloromethyl methyl ether is a known human carcinogen.bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition References Category:Reagents for organic chemistry Category:Protecting groups Category:Glycol ethers Category:IARC Group 1 carcinogens Category:Chloromethyl ethers