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Sigma-Aldrich

Hydrazobenzene

Synonym(s):

N,N′-Diphenylhydrazine, N,N′-Bianiline, NSC 3510

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About This Item

Linear Formula:
C6H5NHNHC6H5
CAS Number:
122-66-7
Molecular Weight:
184.24
Beilstein/REAXYS Number:
639793
EC Number:
204-563-5
MDL number:
MFCD00003012
UNSPSC Code:
12352100
PubChem Substance ID:
24847740
NACRES:
NA.22

form

solid

mp

123-126 °C (lit.)

SMILES string

N(Nc1ccccc1)c2ccccc2

InChI

1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H

InChI key

YBQZXXMEJHZYMB-UHFFFAOYSA-N

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General description

Hydrazobenzene has been prepared by the reduction of azobenzene by SmI(2) in THF.
Hydrazobenzene is an intermediate in the hydrogenation of azoxybenzene to aniline.

Application

Reactant involved in:
  • Insertion reactions with organometallic tantalum complexes
  • Reduction reactions catalyzed by titanium(III) trichloride yielding amines
  • Studying the mechanism of hydrazobenzene rearrangement
  • Reaction with N-heterocyclic stable silylene
  • Synthesis of dimanganese amide hydrazide cluster complexes
  • Iron-mediated hydrazine reductions yielding iron arylimide cubanes

Other Notes

Contains varying amounts of azobenzene

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Chintada Nageswara Rao et al.
The Journal of organic chemistry, 76(22), 9438-9443 (2011-10-19)
The reduction of azobenzene by SmI(2) in THF to give hydrazobenzene was investigated. The kinetics are first order in the substrate and first order in SmI(2). The kinetic order in MeOH is ca. 0.56, and in TFE it is ca.
F Matsui et al.
Journal of pharmaceutical sciences, 72(10), 1223-1224 (1983-10-01)
A high-performance liquid chromatographic method has been developed for the simultaneous determination of azobenzene and hydrazobenzene in phenylbutazone and sulfinpyrazone raw materials and formulations. The drug raw material or formulation is shaken with 1N NaOH and n-hexane and centrifuged. The
S Ohnishi et al.
Free radical research, 32(6), 469-478 (2000-05-08)
Hydrazobenzene is carcinogenic to rats and mice and azobenzene is carcinogenic to rats. Hydrazobenzene is a metabolic intermediate of azobenzene. To clarify the mechanism of carcinogenesis by azobenzene and hydrazobenzene, we investigated DNA damage induced by hydrazobenzene, using 32P-5'-end-labeled DNA
H Taguchi et al.
Analytical biochemistry, 131(1), 194-197 (1983-05-01)
A new fluorometric assay method for quinolinic acid is introduced in this study. Quinolinic acid-hydrazine complex, a stable fluorescent compound, is formed after heating quinolinic acid with hydrazine at 215-220 degrees C for 2 min. Fluorescence excitation and emission maxima
Hydrazobenzene.
Report on carcinogens : carcinogen profiles, 10, 139-140 (2004-08-26)
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