p-Toluenesulfonyl Bromide

Le résumé fourni par la source

[1950-69-2] C7H7BrO2S (MW 235.10) InChI = 1S/C7H7BrO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3 InChIKey = NTSFJZORNYYLFW-UHFFFAOYSA-N (reagent used as a radical cyclization initiator and sulfonating, halogenating reagent) Alternate Name: 4-methylbenzenesulfonyl bromide, tosyl bromide, TsBr. Physical Data: mp 95–96 °C. Solubility: sparingly soluble in H2O; soluble in toluene, benzene, and methylene chloride. Form Supplied in: solid, not commercially available. Analysis of Reagent Purity: melting point; a detailed structural analysis was performed using electron diffraction, MS,1 and IR.2 Preparative Methods: the title reagent can be prepared by the following methods: treatment of tosylsulfonic acid anhydride with HBr in AcOH for 20–30 min;3 reacting p-toluenesul-fonylhydrazide with a mixture of NaBr and NaBrO3 in acidic solution;4 reacting p-toluenesulfonylhydrazide with 2 mol of bromine;5 diazotizing p-aminotoluene in 48% HBr at 3 °C with solid NaNO2 then adding to a mixture of SO2, benzene, CuBr2, and KBr in dioxane;6 and reacting the sodium salt of p-toluenesulfinic acid with bromine.7 Purification: recrystallization from low boiling pet. ether.4 Handling, Storage, and Precautions: not available, but should be similar to tosyl chloride.

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