Chloromethanesulfonyl Chloride

[3518-65-8] CH2Cl2O2S (MW 149.00) InChI = 1S/CH2Cl2O2S/c2-1-6(3,4)5/h1H2 InChIKey = KQDDQXNVESLJNO-UHFFFAOYSA-N (synthesis of chloromethanesulfonates and chloromethanesulfonamides, used for conversion of alcohols into the inverted acetates,2 azides and nitriles,1 and rearrangement of carbon–carbon1 and carbon–oxygen bonds3 under mild conditions, and in electrophilic and radical reactions4) Physical Data: bp 80–81 °C/25 mmHg; d 1.67 g cm−3; nD26 1.4840–1.4850. Solubility: insoluble in H2O; soluble in dichloromethane, pyridine, and most organic solvents. Form Supplied in: colorless liquid; purchased from TCI, E-Merck and Alfa. Preparative Methods: reaction of s-trithiane with chlorine in acetic acid–H2O (20–32%);5, 6 reaction of sodium chloromethanesulfonate with phosphorus pentachloride (79%).7 Handling, Storage, and Precautions: moisture-sensitive, corrosive lachrymator, severe skin and eye irritant, LD50 (rat, oral) 372 mg/kg. Store under nitrogen atmosphere and refrigerator.