1 H ‐Indole‐1‐carbodithioic, 5‐Bromo, Potassium Salt (1:1)

Abstract

[2259877-95-5] C9H5BrKNS2 (MW 310.27) InChI = 1S/C9H6BrNS2.K/c10-7-1-2-8-6(5-7)3-4-11(8)9(12)13;/h1-5H,(H,12,13);/q;+1/p-1 InChIKey = XNBQTAHYWUHBLW-UHFFFAOYSA-M (reagent used as a catalyst for visible-light-driven radical transformations, promoting the formation of radicals from: (i) benzylic or allylic (pseudo)halides and (ii) redox-active radical precursors, including N-hydroxyphthalimide esters, N-alkylpyridinium salts, and hypervalent iodine reagents.) Physical Data: mp 179–185 °C. Solubility: soluble in H2O, DMSO, DMF, DMA, CH3CN. Poor solubility in CH2Cl2, CHCl3, toluene, THF, and insoluble in apolar solvents, such as hexane. Form Supplied in: yellow powder or crystals. Analysis of Reagent Purity: NMR, HRMS, IR. Preparative Methods: the reagent is synthesized by treating 5-bromoindole with potassium tert-butoxide at 0 °C, followed by the addition of carbon disulfide.1 The reagent is also commercially available (more information at https://www.sigmaaldrich.com/ES/es/product/aldrich/907502). Purification: stirred in a 1:1 mixture of diethyl ether and pentane until a suspension of fine yellow powder is observed. The solid is then filtered and dried under high vacuum to obtain a yellow powder. Handling, Storage, and Precautions: usually stored in dark brown bottles and in a moisture-free desiccator since the powder is somewhat hygroscopic. No degradation is observed after several months of storage under these conditions. Use in acidic media generally results in rapid release of CS2 and 5-Br-indole. Treatment with oxidizing agents results in the formation of SS disulfide bonds.