Phenylhydrazine
Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. It is often abbreviated as PhNHNH2.
Chemical properties
Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air. Phenylhydrazine is miscible with ethanol, diethyl ether, chloroform, and benzene. It is sparingly soluble in water.
Preparation
Phenylhydrazine is prepared by oxidizing aniline with sodium nitrite in the presence of hydrogen chloride to form the diazonium salt, which is subsequently reduced using sodium sulfite in the presence of sodium hydroxide to form the final product.
History
Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875. He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones with the sugar aldehyde. He also demonstrated in this first paper many of the key properties recognized for hydrazines.
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