2,4,6-Triisopropylbenzenesulfonylhydrazide

Abstract

[39085-59-1] C15H26N2O2S (MW 298.50) InChI = 1S/C15H26N2O2S/c1-9(2)12-7-13(10(3)4)15(20(18,19)17-16)14(8-12)11(5)6/h7-11,17H,16H2,1-6H3 InChIKey = UGRVYFQFDZRNMQ-UHFFFAOYSA-N (used as a diazene equivalent;3 condensed with ketones and aldehydes to form hydrazones that can be converted into reactive intermediates such as diazoalkanes, carbenes,13 carbenium ions, alkyllithiums,9 or umpolung synthons) Alternate Name: trisyl hydrazide; TPSH. Physical Data: mp 121–122 °C (dec). Solubility: sol virtually all ethereal, halogenated, protic, and aprotic solvents; insol water and hydrocarbon solvents. Analysis of Reagent Purity: NMR, IR, TLC. Preparative Methods: may be prepared in 96% yield by treating commercially available 2,4,6-triisopropylbenzenesulfonyl chloride2 with hydrazine hydrate in THF,3, 4 being careful to keep the reaction and workup temperatures below or around 0 °C. The solid can be dried in vacuo over P2O5 for 24 h. Handling, Storage, and Precautions: decomposes rapidly in solution at rt to diazene, particularly under basic or neutral conditions; acid retards this degradation significantly. It is stable in solid form at −20 °C for months and may be freed from acidic impurities as described in the literature.3 2,4,6-Triisopropylbenzenesulfonylhydrazide is a toxic, potentially flammable solid which should be handled with gloves under an inert atmosphere.