[4972-31-0] C11H15NOS (MW 209.31) InChI = 1S/C11H15NOS/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8H,2,5-6,9-10H2 InChIKey = LBRJCAJLGAXDKP-UHFFFAOYSA-N (reagent used in combination with trifluoromethanesulfonic anhydride to form a powerful electrophilic salt capable of activating thioglycosides and selenoglycosides for the construction of glycosidic linkages; can also be used for the C-alkylation of β-ketoester enolates) Alternate Name: BSP. Physical Data: mp 84–85 °C. Solubility: soluble in dichloromethane, diethyl ether, toluene, and most organic solvents. Form Supplied in: off-white solid. Analysis of Reagent Purity: melting point, NMR spectrum. Preparative Methods: a solution of PhSOCl (58.0 g, 0.365 mol) in anhydrous diethyl ether (200 mL) is slowly added to a cooled solution (5 °C) of piperidine (72 mL, 0.73 mmol) in anhydrous diethyl ether (200 mL). The reaction mixture is stirred at room temperature for 1 h, filtered, and then concentrated under reduced pressure. The solid residue is triturated with hexanes to give 1-benzenesulfinyl piperidine (53.4 g, 70%). Handling, Storage, and Precautions: unknown toxicity. Should be used within a fumehood.