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100-63-0 - Phenylhydrazine, 97% - A11246 - Alfa Aesar

A11246 Phenylhydrazine, 97%

Codice CAS
100-63-0
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
50g 17,70
250g 60,00
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Phenylhydrazine, 97%

MDL
MFCD00007573
EINECS
202-873-5

Proprietà chimiche

Formula
C6H8N2
Peso formula
108.14
Punto di fusione
18-20°
Punto di ebollizione
238-241°
Punto di infiammabilità
88°(190°F)
Densità
1.099
Indice di rifrazione
1.6065
Sensibilità
Air & Light Sensitive
Solubilità
Soluble in dilute acids.

Applicazioni

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.

Note

Air and light sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.

Letteratura

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.; Mar’yasov, 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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): 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.

Dichiarazioni precauzionali: P210u-P260-P301+P310a-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER/doctor 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.

Altri riferimenti

Merck
14,7293
Beilstein
606080
Classe di rischio
6.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2928.00
TSCA
Yes
RTECS
MV8925000

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