2-Chloroethyl Chloromethyl Ether

Abstract

[1462-33-5] C3H6Cl2O (MW 128.98) InChI = 1S/C3H6Cl2O/c4-1-2-6-3-5/h1-3H2 InChIKey = LUTWEKBTDWRTSE-UHFFFAOYSA-N (reagent for cyclopropanol synthesis;1, 2 formaldehyde equivalent in hydroxymethylation of Grignard reagents;3 used for protection of indoles4) Alternate Name: 1-chloro-2-(chloromethoxy)ethane. Physical Data: bp 145–147 °C (66–68 °C/22 mmHg);3 d 1.28 g cm−3.5 Solubility: sol most commonly used organic solvents including ethereal (THF, diethyl ether), halogenated (CH2Cl2, CHCl3, CCl4), and hydrocarbon solvents; incompatible with alcohol solvents. Analysis of Reagent Purity: best ascertained by 1H NMR [(300 MHz, CDCl3/TMS) δ 3.96 (t, J = 5.7 Hz, 2 H), 3.96 (t, J = 5.7 Hz, 2 H), 5.53 (s, 2 H)].3 Preparative Method: most conveniently prepared by reaction of 2-chloroethanol and 1,3,5-trioxane with HCl(g) at 0 °C (1.0 mol scale, 66% yield).3, 6 Purification: by distillation. Handling, Storage, and Precautions: chloromethyl ethers are recognized carcinogens.7 Preparation and handling of the reagent should be carried out in an efficient fume hood, and skin contact should be avoided. Chloromethyl ethers are also moisture-sensitive and should be stored and transferred under inert atmosphere. Excess reagent should be hydrolyzed in water before removing from the fume hood.3