|Jmol-3D images||Image 1|
|Molar mass||108.14 g/mol|
|Melting point||19.5 °C
24 °C for hemihydrate
|Boiling point||243.5 °C (decomposition)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. Organic chemists abbreviate the compound as PhNHNH2.
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.
Phenylhydrazine is prepared by reducing 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.
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.
The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.
- Merck Index, 11th Edition, 7264.
- Pure component properties
- Merck Index of Chemicals and Drugs, 9th ed. monograph 7098
- Fischer, E. (1875) "Ueber aromatische Hydrazinverbindungen," Berichte der deutschen chemischen Gesellschaft, 8: 589-594.
- Streitweiser, Andrew Jr.; Heathcock, Clayton H. (1976). Introduction to Organic Chemistry. Macmillan. ISBN 0-02-418010-6.
- Phenylhydrazines at the US National Library of Medicine Medical Subject Headings (MeSH)
- Additional chemical properties of phenylhydrazine
- CDC - NIOSH Pocket Guide to Chemical Hazards