P-Toluenesulfonyl Hydrazide on:
[Wikipedia]
[Google]
[Amazon]
''p''-Toluenesulfonyl hydrazide is the
Tosylhydrazides can be installed by nucleophilic attack and later removed by base. It thus provides a way to covert C-Cl to C-H.
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
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 thehydrazone
Hydrazones are a class of organic compounds with the structure . They are related to ketones and aldehydes by the replacement of the oxygen =O with the = functional group. They are formed usually by the action of hydrazine on ketones or aldehydes. ...
s:
:CH3C6H4SO2NHNH2 + R2C=O → CH3C6H4SO2NHN=CR2 + H2O
Upon heating in solution, it degrades, releasing diimide
Diimide, also called diazene or diimine, is a compound having the formula (NH)2. It exists as two geometric isomers, ''E'' (''trans'') and ''Z'' (''cis''). The term diazene is more common for organic derivatives of diimide. Thus, azobenzene is ...
(N2H2), a useful reducing agent. Triisopropylbenzenesulfonylhydrazide is far more useful for this reaction.
Synthesis
Toluenesulfonyl hydrazide is prepared by the reaction of atoluenesulfonyl chloride
4-Toluenesulfonyl chloride (''p''-toluenesulfonyl chloride, toluene-''p''-sulfonyl chloride) is an organic compound with the formula CH3C6H4SO2Cl. This white, malodorous solid is a reagent widely used in organic synthesis. Abbreviated TsCl or To ...
with hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine ...
:
:CH3C6H4SO2Cl + 2 NH2NH2 → CH3C6H4SO2NHNH2 + + H2NH3l
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.
References