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P26252

Sigma-Aldrich

Phenylhydrazine

97%

Synonym(s):

Hydrazinobenzene, Monophenylhydrazine

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About This Item

Linear Formula:
C6H5NHNH2
CAS Number:
100-63-0
Molecular Weight:
108.14
Beilstein:
606080
EC Number:
202-873-5
MDL number:
MFCD00007573
UNSPSC Code:
12352100
PubChem Substance ID:
24898342
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

200

vapor pressure

<0.1 mmHg ( 20 °C)

Assay

97%

autoignition temp.

345 °F

refractive index

n20/D 1.607 (lit.)

bp

238-241 °C (lit.)

mp

18-21 °C (lit.)

density

1.098 g/mL at 25 °C (lit.)

SMILES string

NNc1ccccc1

InChI

1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2

InChI key

HKOOXMFOFWEVGF-UHFFFAOYSA-N

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Application

Phenylhydrazine can be used as a reactant in the synthesis of:
  • 4, 4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s by reacting with aryl aldehydes and acetoacetates in presence of N-bromo sulfonamide as a catalyst via one-pot pseudo-five-component condensation.
  • Thiazolidinones by treating with mercaptoacetic acid and aldehydes or ketones.
  • 5-[3,3,3-trifluoro-2-(phenylhydrazono)propyl]-1-phenyl-1H-pyrazole-3-carboxylic acid by reacting with 6-(trifluoromethyl)comanic acid.

It can be also used as a precursor for the preparation of selective carboxymethylated products at N-1 and N-2 by reacting with dimethyl carbonate (DMC) in the presence of a Bronsted base and metal salts as a catalyst.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Carc. 1B - Eye Irrit. 2 - Muta. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Erika Lattova et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 793(1), 167-179 (2003-07-26)
A well-known reaction of carbonyl compounds with phenylhydrazine has been applied to saccharides, providing increased sensitivity for mass spectrometric (MS) and ultraviolet (UV) detection during high-performance liquid chromatographic (HPLC) separations. After a simple derivatization procedure for 1 h at 70
Tandem cyclocondensation-Knoevenagel-Michael reaction of phenyl hydrazine, acetoacetate derivatives and arylaldehydes
Khazaei A, et al.
New. J. Chem., 38(11), 5287-5292 (2014)
Regioselective solvent-sensitive reactions of 6-(trifluoromethyl) comanic acid and its derivatives with phenylhydrazine
Usachev BI, et al.
Tetrahedron Letters, 50(31), 4446-4448 (2009)
Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine
Rosamilia AE, et al.
The Journal of Organic Chemistry, 73(4), 1559-1562 (2008)
Efficient solvent-free synthesis of thiazolidin-4-ones from phenylhydrazine and 2, 4-dinitrophenylhydrazine
Neuenfeldt PD, et al.
Tetrahedron Letters, 51(23), 3106-3108 (2010)
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