Phenylhydrazine

Chembox new
Name = Phenylhydrazine
Reference ="Merck Index", 11th Edition, 7264.] [ [http://www.cheric.org/kdb/kdb/hcprop/showprop.php?cmpid=1470 Pure component properties] ]
ImageFile = phenylhydrazine.png ImageSize = 100px
ImageName = Phenylhydrazine
ImageFileL1 = Phenylhydrazine-3D-balls.png ImageSizeL1 = 100px
ImageNameL1 = Ball-and-stick model of phenylhydrazine
ImageFileR1 = Phenylhydrazine-3D-vdW.png ImageSizeR1 = 100px
ImageNameR1 = Space-filling model of phenylhydrazine
IUPACName = Phenylhydrazine
OtherNames = Hydrazinobenzene
Section1 = Chembox Identifiers
CASNo = 100-63-0
SMILES = c1ccccc1NN
Section2 = Chembox Properties
Formula = C₆H₈N₂
MolarMass = 108.14 g/mol
Density = 1.0978 g/cm³
MeltingPt = 19.5 °C
24 °C for hemihydrate
BoilingPt = 243.5 °C ("decomposition")
Section7 = Chembox Hazards
NFPA-H = 3
NFPA-F = 2
NFPA-R = 3

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

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. 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."Merck Index of Chemicals and Drugs, 9th ed." monograph 7098]

History

Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875. [Fischer, E. "Ueber aromatische Hydrazinverbindungen" Ber. Dtsch. Chem. Ges., 1875, band 8, 589-594.] 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. [cite book|author=Streitweiser, Andrew Jr.; Heathcock, Clayton H.|title=Introduction to Organic Chemistry|publisher=Macmillan|date=1976|isbn=0-02-418010-6]

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

afety

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

ee also

*Fischer indole synthesis

References

External links

*
* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7516 PubChem]
* [http://www.chemicalland21.com/lifescience/agro/PHENYL%20HYDRAZINE.htm Additional chemical properties if phenylhydrazine]