Phenyl hydrazine

Phenylhydrazine

Names
IUPAC name Phenylhydrazine
Other names Hydrazinobenzene
Identifiers
CAS Number	100-63-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27924 Y
ChemSpider	7235 Y
ECHA InfoCard	100.002.612
KEGG	C02304 Y
PubChem CID	7516
UNII	064F424C9K N
InChI InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2 Y Key: HKOOXMFOFWEVGF-UHFFFAOYSA-N Y InChI=1/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2 Key: HKOOXMFOFWEVGF-UHFFFAOYAN
SMILES NNc1ccccc1
Properties
Chemical formula	C6H8N2
Molar mass	108.14 g/mol
Appearance	Colorless to pale-yellow liquid or solid
Odor	faint, aromatic
Density	1.0978 g/cm3
Melting point	19.5 °C (67.1 °F; 292.6 K) (24 °C for hemihydrate)
Boiling point	243.5 °C (470.3 °F; 516.6 K) (decomposition)
Vapor pressure	0.04 mmHg (25°C)
Magnetic susceptibility (χ)	-67.82·10−6 cm3/mol
Hazards
NFPA 704	2 3 3
Flash point	88 °C; 190 °F; 361 K
Lethal dose or concentration (LD, LC):
LD50 (median dose)	188 mg/kg (rat, oral) 175 mg/kg (mouse, oral) 80 mg/kg (rabbit, oral) 80 mg/kg (guinea pig, oral) 200-250 mg/kg (dog, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 5 ppm (22 mg/m3) [skin]
REL (Recommended)	Ca C 0.14 ppm (0.6 mg/m3) [2-hr] [skin]
IDLH (Immediate danger)	Ca [15 ppm]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Phenylhydrazine is the chemical compound with the formula C₆H₅NHNH₂. It is often abbreviated 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 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.

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.

Phenyl-hydrazine is used to prepare indoles via 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.