p-Toluenesulfonyl hydrazide is the organic compound with the formula CH3C6H4SO2NHNH2. It is a white solid that is soluble in many organic solvents but not water or alkanes. It is a reagent in organic synthesis.
Reactions
With ketones and aldehydes, it condenses to give the hydrazones: CH3C6H4SO2NHNH2 + R2C=O → CH3C6H4SO2NHN=CR2 + H2O
Upon heating in solution, it degrades, releasing diimide (N2H2), a useful reducing agent. Triisopropylbenzenesulfonylhydrazide is far more useful for this reaction.
Synthesis
Toluenesulfonyl hydrazide is prepared by the reaction of a toluenesulfonyl chloride with hydrazine: CH3C6H4SO2Cl + 2 NH2NH2 → CH3C6H4SO2NHNH2 + + [NH2NH3]Cl
Reactions
Tosylhydrazides can be installed by nucleophilic attack and later removed by base. It thus provides a way to covert C-Cl to C-H.