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Phenyl hydrazine is involved in Fischer indole synthesis to prepare indoles, which find application as intermediates in the pharmaceuticals particularly for the tryptamine drug. In analytical chemistry, it is used to differentiate and separate sugars by forming phenyhydrazones. It is used as an N-protecting reagent and for cleavage of phthaloyl group.
Derivatizing agent for the conversion of carbonyl compounds to their phenylhydrazones best known as intermediates in the Fischer indole synthesis, by cyclization under acidic conditions with loss of ammonia. The classical reagent is anhydrous ZnCl2: Org. Synth. Coll., 3, 725 (1976). For reviews, see: Chem. Rev., 63, 373 (1963); 69, 227 (1969); Tetrahedron, 36, 161 (1980); Org. Prep. Proced. Int., 25, 609 (1993). Milder cyclization conditions are sometimes effective, e.g.: dilute H2SO4: J. Org. Chem., 59, 3738 (1994); PCl3: J. Chem. Soc., Chem. Commun., 563 (1981); Tetrahedron, 41, 4615 (1985). Cyclohexanone phenylhydrazone gives tetrahydrocarbazole on heating in acetic acid: Org. Synth. Coll., 4, 884 (1963).
Methods used for the cleavage of phenylhydrazones include exchange by refluxing with acetone: J. Org. Chem., 40, 3302 (1975), or oxidative cleavage by Fe(NO3)3 on a clay support: Synthesis, 439 (1985).
Wang, L.; Wang, P.; Liu, Y.; Zheng, L.; Sun, Q.; Qiu, S.; Liu, C. Effects of phenylhydrazine-4-sulfonic acid on the reduction of GO and preparation of hydrophilic graphene with broad pH stability and antioxidant activity. RSC Adv. 2015, 5 (48), 38696-38705.
Gein, V. L.; Maryasov, M. A. Reactions of 5-aryl-4-(hetaren-2-ylcarbonyl)-3-hydroxy-1-(1, 3-thiazol-2-yl)-2, 5-dihydro-1H-pyrrol-2-ones with hydrazine, phenylhydrazine, and hydroxylamine. Russ. J. Org. Chem. 2015, 51 (1), 110-115.
Gefahrenhinweise (EU): H227-H301-H311-H331-H315-H319-H317-H341-H350-H372
Combustible liquid. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. Suspected of causing genetic defects. May cause cancer. Causes damage to organs through prolonged or repeated exposure.
Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.