Phenylhydrazine
Title: Phenylhydrazine
CAS Registry Number: 100-63-0
Additional Names: Hydrazinobenzene
Molecular Formula: C6H8N2
Molecular Weight: 108.14
Percent Composition: C 66.64%, H 7.46%, N 25.90%
Line Formula: C6H5NHNH2
Literature References: Prepd by diazotizing aniline with NaNO2 and HCl, then treating the soln with Na2SO3 followed by NaOH: Fischer, Anleitung zur Darstellung organischer Präparate (Braunschweig, 10th ed., 1922) p 23; Coleman, Org. Synth. 2, 71 (1922), coll. vol. I (2nd ed., 1941) p 442. Mechanism of oxidative hemolysis of erythrocytes: B. Goldberg, A. Stern, Mol. Pharmacol. 13, 832 (1977); B. Vilsen, H. Nielsen, Biochem. Pharmacol. 33, 2739 (1984). Review of interaction with hemoglobin: M. D. Shetlar, H. A. O. Hill, Environ. Health Perspect. 64, 265-281 (1985).
Properties: Monoclinic prisms or oil. Turns yellow to dark red on exposure to air and light. Faint aromatic odor. d420 1.0978; mp 19.5°; bp760 243.5° (dec); bp100 173.5°; bp40 148.2°; bp20 131.5°; bp10 115.8°; bp5 101.6°; bp1.0 71.8°; nD20.3 1.60813. Weak base, pK (15°): 8.79. Miscible with alcohol, ether, chloroform, benzene. Sparingly sol in water, petr ether; sol in dil acids. Forms a hemihydrate, mp 24°. Keep well closed and protected from light.
Melting point: mp 19.5°; mp 24°
Boiling point: bp760 243.5° (dec); bp100 173.5°; bp40 148.2°; bp20 131.5°; bp10 115.8°; bp5 101.6°; bp1.0 71.8°
pKa: pK (15°): 8.79
Index of refraction: nD20.3 1.60813
Density: d420 1.0978
 
Derivative Type: Hydrochloride
CAS Registry Number: 59-88-1
Molecular Formula: C6H8N2.HCl
Molecular Weight: 144.60
Percent Composition: C 49.84%, H 6.27%, N 19.37%, Cl 24.52%
Literature References: Prepn: Fischer, Ann. 190, 83 (1878); Brunner, Eiermann, Ber. 31, 1406 (1898); Rüetschi, Trümpler, Helv. Chim. Acta 36, 1649 (1953); Hupfer, DE 1143825 (1963 to Hoechst).
Properties: Leaflets from alc, mp 243-246° (slight browning). Sublimes. Freely sol in water; sol in alcohol. Practically insol in ether.
Melting point: mp 243-246° (slight browning)
 
CAUTION: Potential symptoms of overexposure are skin sensitization, hemolytic anemia, dyspnea and cyanosis; jaundice; kidney damage; vascular thrombosis. Potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 250. See also Patty's Industrial Hygiene and Toxicology vol. 2A, G. D. Clayton, R. E. Clayton, Eds. (Wiley-Interscience, New York, 3rd ed., 1981) pp 2792-2795, 2804-2805.
Use: Manuf dyes, antipyrine, nitron (a stabilizer for explosives); reagent for sugars, aldehydes, ketones.
Therap-Cat: Hemolytic.
Keywords: Hemolytic.

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