Phenylhydrazine

Phenylhydrazine[1][2]
IUPAC name

Phenylhydrazine
Other names

Hydrazinobenzene
Identifiers
CAS number 100-63-0 Y
PubChem 7516
ChemSpider 7235 Y
KEGG C02304 Y
ChEBI CHEBI:27924 Y
ChEMBL CHEMBL456807 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H8N2
Molar mass 108.14 g/mol
Density 1.0978 g/cm3
Melting point

19.5 °C
24 °C for hemihydrate
Boiling point

243.5 °C (decomposition)
Hazards
NFPA 704
2
3
3
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

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.

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.[3]

History

Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875.[4] 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.

Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugars in order to render the differing sugars easily separable from each other.[5]

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. ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 7098
  4. ^ Fischer, E. "Ueber aromatische Hydrazinverbindungen" Ber. Dtsch. Chem. Ges., 1875, band 8, 589-594.
  5. ^ Streitweiser, Andrew Jr.; Heathcock, Clayton H. (1976). Introduction to Organic Chemistry. Macmillan. ISBN 0-02-418010-6. 

External links