''p''-Toluenesulfonyl hydrazide is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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.

Synthesis

Toluenesulfonyl hydrazide is prepared by the reaction of a

toluenesulfonyl 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 hazardous unless handled in solution as, for example, hydraz ...

: :

Reactions

: Tosylhydrazides can be installed by nucleophilic attack and later removed by base. It thus provides a way to convert C-Cl to C-H. With ketones and aldehydes, it condenses to give the

hydrazone 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 HN=NH. 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 an ...

(N₂H₂), a useful reducing agent. Triisopropylbenzenesulfonylhydrazide is far more useful for this reaction.

Use

The compound is an important reagent in organic synthesis, serving as a source of reactive

and its subsequent chemical reactions. It condenses with

ketones In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

and

aldehydes In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

to form

hydrazones 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. ...

, which can be further transformed into reactive intermediates such as

diazo compounds In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds ...

carbenes In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may ...

. ''N''-heterocycles can be synthesized through 1,3-dipolar cycloaddition reactions. Ketone hydrazones are defunctionalized using mild reagents in a modified Wolff-Kishner reaction. A notable commercial application of this compound is as a foaming reagent for polymers.Baoming, X.; Huan, H.; Yangyang, H.; Jie, Z.; Zhishan P.; Qiang, T.: ''Research progress on the synthesis and application of the sulfonyl hydrazides blowing agent'' in

Chemistry World ''Chemistry World'' is a monthly chemistry news magazine published by the Royal Society of Chemistry. The magazine addresses current events in the world of chemistry including research, international business news and government policy as it affe ...

56 (2015) 125–128.

References

{{DEFAULTSORT:Toluenesulfonyl hydrazide, p- Hydrazides