5-Thianthrenyl-5-ylium Perchlorate

[35787-71-4] C12H8ClO4S2 (MW 315.77) InChI = 1S/C12H8S2.ClHO4/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10;2-1(3,4)5/h1-8H;(H,2,3,4,5)/q+1;/p-1 InChIKey = RABXTOXCGQBKCR-UHFFFAOYSA-M (reagent commonly used as a one-electron oxidant) Alternate Names: thianthrene cation radical perchlorate, thianthrenium perchlorate. Solubility: sol in sulfuric acid, nitromethane, acetonitrile, 1,2-dichloroethane. Form Supplied in: dark, reddish brown/purple crystals; not available commercially. Analysis of Reagent Purity: UV–Vis (e546(acetonitrile) = 8.5 × 103); 5-line ESR spectrum in acetonitrile (g = 2.0087);1 iodimetric assay (92%).2 Preparative Methods: prepared by combining a solution of thianthrene (Th) in CCl4 with HClO4 in acetic anhydride and stirring at room temperature overnight.1, 3 The resulting crystals are used without further purification; recrystallization is unsuccessful due to low solubility.1 Handling, Storage, and Precautions: shock sensitive. A freshly made 1–2 g batch exploded violently after being dried and transferred from a sintered-glass filter to a Petri dish. It is advised that the reagent be synthesized in small amounts (ca. 100 mg) and filtered through glass fiber paper and used immediately. Friction caused by glass stirring rods can result in detonation. To avoid decomposition, the reagent should be used without long delay, away from moisture.