Phenylhydrazine

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 reacting 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 Hermann 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 known as osazones with the sugar aldehyde. He also demonstrated in this first paper many of the key properties recognized for hydrazines.

Uses

Phenylhydrazine is used to prepare indoles by the Fischer indole synthesis, which are intermediates in the synthesis of various dyes and pharmaceuticals.

Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugars in order to render the differing sugars easily separable from each other.

This molecule is also used to induce acute hemolytic anemia in animal models.

Safety

Exposure to phenylhydrazine may cause contact dermatitis, hemolytic anemia, and liver damage.

References

References

1. ''Merck Index'', 11th Edition, '''7264'''.
2. [https://web.archive.org/web/20020802222945/http://www.cheric.org/kdb/kdb/hcprop/showprop.php Pure component properties]
3. {{PGCH. 0499
4. {{IDLH. 100630. Phenylhydrazine
5. (2004). "Phenylhydrazines in the cultivated mushroom (Agaricus bisporus)". Nordic Council of Ministers.
6. ''Merck Index of Chemicals and Drugs, 9th ed.'' monograph 7098
7. Nobel Committee [https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html Emil Fischer - Biographical]
8. Fischer, E. (1875) [http://gallica.bnf.fr/ark:/12148/bpt6k90680z/f589.zoom.langEN "Ueber aromatische Hydrazinverbindungen,"] ''Berichte der deutschen chemischen Gesellschaft'', '''8''': 589-594.
9. (1976). "Introduction to Organic Chemistry". Macmillan.