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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.
Hazard Statements: H227-H301-H311-H315-H317-H319-H331-H335-H341-H350-H372
Combustible liquid. Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye irritation. Toxic if inhaled. May cause respiratory irritation. Suspected of causing genetic defects. May cause cancer. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P235-P260-P264b-P270-P271-P272-P280-P281-P301+P310-P302+P352-P304+P340-P305+P351+P338-P308+P313-P311-P312-P330-P333+P313-P337+P313-P361-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation or rash occurs: If eye irritation persists: Remove/Take off immediately all contaminated clothing. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant