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Phenylhydrazine



Phenylhydrazine[1][2]
Chemical name Phenylhydrazine
Other names Hydrazinobenzene
Chemical formula C6H8N2
Molecular mass 108.14 g/mol
CAS number [100-63-0]
Density 1.0978 g/cm3
Melting point 19.5 °C
24 °C for hemihydrate
Boiling point 243.5 °C (decomposition)
SMILES c1ccccc1NN
NFPA 704
2
3
3
 
Disclaimer and references

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

Additional recommended knowledge

Contents

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

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.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenylhydrazine". A list of authors is available in Wikipedia.
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