phenylhydrazine

• ChemBase ID: 103452
• Molecular Formular: C6H8N2
• Molecular Mass: 108.14112
• Monoisotopic Mass: 108.06874827
• SMILES: NNc1ccccc1
• Canonical SMILES: NNc1ccccc1
• InChI: InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2
• InChIKey: HKOOXMFOFWEVGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenylhydrazine
• IUPAC Traditional name: phenylhydrazine
• Synonyms: Phenylhydrazine; Monophenylhydrazine; Hydrazinobenzene; PHENYLHYDRAZINE; 苯肼

Database IDs

• CAS Number: 100-63-0
• EC Number: 202-873-5
• MDL Number: MFCD00007573
• Beilstein Number: 606080
• Merck Index: 147293
• PubChem SID: 24887154; 24898342; 24887153; 162091326
• PubChem CID: 7516
• CHEBI ID: 27924
• CHEMBL: 456807
• Chemspider ID: 7235
• KEGG ID: C02304
• Wikipedia Title: Phenylhydrazine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.1338776
• LogD (pH = 7.4): 1.3610642
• Log P: 1.3648884
• Molar Refractivity: 35.7647 cm^3
• Polarizability: 12.905999 Å^3
• Polar Surface Area: 38.05 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in dilute acids
• Melting Point: 18-20°C; 18-21 °C(lit.); 19.5 °C; 19.5 °C; 24 °C for hemihydrate
• Boiling Point: 238-241 °C(lit.); 238-241°C; 243 °C (with decomposition); 243.5 °C (decomposition)
• Flash Point: 192.2 °F; 88.8°C; 88°C(190°F); 89 °C
• Auto Ignition Point: 345 °F
• Density: 1.0978 g/cm^3; 1.098 g/mL at 25 °C(lit.); 1.099; 1.10 at 20 °C (water = 1)
• Refractive Index: 1.6065; n20/D 1.607(lit.)
• Vapor Pressure: <0.1 mm Hg at 30 °C; <0.1 mmHg ( 20 °C)
• Vapor Density: 3.70 (air = 1); 4.3 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Protect from light
• Storage Warning: Air & Light Sensitive
• RTECS: MV8925000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2572; UN2572
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 3X
• Risk Statements: 45-23/24/25-36/38-43-48/23/24/25-50-68; 45-23/24/25-36/38-43-48/23/24/25-68-50; R:23/24/25-36-50
• Safety Statements: 53-45-61; S:28-45-61
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  2

  3

  3
• GHS Hazard statements: H301-H311-H315-H317-H319-H331-H341-H350-H372-H400; H301-H311-H331-H315-H319-H317-H350-H372-H341-H400-H227
• GHS Precautionary statements: P201-P261-P273-P280-P301 + P310-P305 + P351 + P338; P210-P301+P310-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2572 6.1/PG 2

Product Information

• Purity: ≥95.0% (GC); 97%
• Grade: purum; purum p.a.
• Linear Formula: C6H5NHNH2

DETAILS

MP Biomedicals - 02151837

Free Base Used as N-protecting reagent and for cleavage of phthaloyl group. 1 ml = approx. 1.10 g

MP Biomedicals - 05217394

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P26252

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 78670

Application
for spectrophotometric determination of Al, Cr, Mo, Ti, Zr

Toronto Research Chemicals - P335075

An aryl hydrazine used in the preparation of various dyes and pharmaceutical compounds. It is used in the investigation of oligosaccharides as well as the structure of photosystem II.

REFERENCES

• Lattova, E. et al.: Meth. Mol. Biol., 534, 65 (2009)
• Anderson, L.B. et al.: J. Biol. Chem., 275, 4920 (2009)
• 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).