Phenylhydrazine

Phenylhydrazine is the chemical compound with the formula C₆H₅NHNH₂. Organic chemists abbreviate the compound PhNHNH₂.

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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.^[1] Phenylhydrazine is miscible with ethanol, diethyl ether, chloroform, and benzene. It is sparingly soluble in water.

History

Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875.^[3] 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.

Uses

Phenylhydrazine is used in preparation of indoles which are intermediates in the synthesis of various dyes and pharmaceuticals.

The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.

Safety

Exposure to phenylhydrazine may cause contact dermatitis, hemolytic anemia, and liver and kidney injury.^[1]

See also

• Fischer indole synthesis

References

1. ^ ^{a b c} Merck Index, 11th Edition, 7264.
2. ^ Pure component properties
3. ^ Fischer, E. "Ueber aromatische Hydrazinverbindungen" Ber. Dtsch. Chem. Ges., 1875, band 8, 589-594.