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

A11246 Phenylhydrazine, 97%

CAS Number
100-63-0
Synonyms

Size Price ($) Quantity Availability
50g 15.39
250g 32.96
1000g 91.16
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Phenylhydrazine, 97%

MDL
MFCD00007573
EINECS
202-873-5

Chemical Properties

Formula
C6H8N2
Formula Weight
108.14
Melting point
18-20°
Boiling Point
238-241°
Flash Point
88°(190°F)
Density
1.099
Refractive Index
1.6065
Sensitivity
Air & Light Sensitive
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: 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.

Precautionary Statements: 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.

Other References

Merck
14,7293
Beilstein
606080
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2928.00
TSCA
Yes
RTECS
MV8925000

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