Phenylselenium Trichloride

Abstract

[42572-42-9] C6H5Cl3Se (MW 261.43) InChI = 1S/C6H5Cl3Se/c7-10(8,9)6-4-2-1-3-5-6/h1-5H InChIKey = QMSNYYFZJWJFSV-UHFFFAOYSA-N (chlorinating agent used for introducing unsaturation via selenoxide elimination) Physical Data: mp 133–134 °C (dec). Solubility: soluble in acetonitrile and DMSO; slightly soluble in methylene chloride and chloroform; insoluble in hexanes, diethyl ether and carbon disulfide. Form Supplied in: pale yellow solid; limited commercial availability. Analysis of Reagent Purity: NMR. Preparative Methods: has been prepared by the treatment of diphenyl diselenide, phenylselenium tribromide, benzeneselenenyl cyanide, or benzeneselenenyl bromide with chlorine(g).1, 2 Larger scale synthesis via chlorination of diphenyl diselenide and benzeneselenol with sulfuryl chloride or the treatment of benzeneseleninic acid with thionyl chloride is preferred.3-5 Purification: recrystallization from benzene, recovery increased in the presence of gaseous HCl or carbon disulfide.2 Handling, Storage, and Precautions: unstable in air, may be prepared immediately prior to use or stored dry at freezing temperatures (−20 °C) under inert atmosphere. Caution: organoselenium compounds may be odorous and/or toxic. Use personal protective equipment and handle in a fume hood.