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

A11246 Phenylhydrazine, 97%

Numéro CAS
100-63-0
Synonymes

Dimensions Prix ($) Quantité Disponibilité
50g 17,70
250g 33,10
1000g 91,60
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Phenylhydrazine, 97%

MDL
MFCD00007573
EINECS
202-873-5

Propriétés chimiques

Formule
C6H8N2
Poids formulaire
108.14
Point de fusion
18-20°
Point d'ébullition
238-241°
Point d'éclair
88°(190°F)
Densité
1.099
Indice de réfraction
1.6065
Sensibilité
Air & Light Sensitive
Solubilité
Soluble in dilute acids.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H311-H331-H315-H319-H317-H350-H372-H341-H400-H227

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. May cause cancer. Causes damage to organs through prolonged or repeated exposure. Suspected of causing genetic defects. Very toxic to aquatic life. Combustible liquid.

Mentions de prudence: P210-P260-P201-P261-P273-P301+P310-P305+P351+P338-P361-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,7293
Beilstein
606080
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2928.00
TSCA
Yes
RTECS
MV8925000

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