Abstract

[2567792-04-3] C4H9NO2S (MW 135.2) InChI = 1S/C4H9NO2S/c1-4(2,3)7-5-8-6/h1-3H3 InChIkey = QNDHWAYLAJVRCB-UHFFFAOYSA-N (used as a sulfonimidoylation reagent for the synthesis of aza-sulfur compounds) Alternative Names: O-(tert-butyl)-N-sulfinylhydroxylamine, (tert-butoxyimino)-λ4-sulfanone, t-BuONSO, and (tert-butoxy)(sulfinylidene)amine. Physical Data: bp 75 °C (40 mbar).1 Solubility: miscible with common organic solvents. Form Supplied in: colorless liquid. Analysis of Reagent Purity: spectroscopic data: IR, Raman, NMR (1H, 13C).1 Preparative Method: t-BuONSO is prepared from the dropwise addition of SOCl2 to t-BuONH2·HCl in the presence of Et3N at 0 °C in anhydrous CH2Cl2. After stirring the reaction for 1 h, diethyl ether is added, and the solid Et3N·HCl salt is removed by filtration with a short pad of Celite. Removal of the solvent and distillation of the crude material at 75 °C (40 mbar) affords the pure product. Purification: distillation. Handling, Storage, and Precautions: t-BuONSO is air and moisture insensitive, hence easily handled under ambient conditions. For long-term storage, it is kept at −20 °C in a freezer under an inert atmosphere. Hydrolysis of t-BuONSO can potentially result in the evolution of toxic SO2.

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