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126721

Sigma-Aldrich

Hydrazobenzene

Sinónimos:

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

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About This Item

Fórmula lineal:
C6H5NHNHC6H5
Número de CAS:
122-66-7
Peso molecular:
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

Quality Level

200

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

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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.
Darol E Dodd et al.
International journal of toxicology, 31(6), 564-571 (2012-11-09)
Male F344 rats were exposed to hydrazobenzene (HZB) by dietary feed at concentrations of 0, 5, 20, 80, 200, or 300 ppm for 5 days, 2 weeks, 4 weeks, or 13 weeks duration. End points evaluated included clinical observations, body
Hydrazobenzene.
Report on carcinogens : carcinogen profiles, 10, 139-140 (2004-08-26)
H Fabre et al.
Journal of pharmaceutical sciences, 73(12), 1706-1709 (1984-12-01)
A high-performance liquid chromatographic method was developed for the simultaneous determination of azobenzene, hydrazobenzene, and four other decomposition products in phenylbutazone injectable formulations. Separation was achieved on a C18 column, with 0.1 M Tris-citrate buffer (pH 5.25) and acetonitrile (52:48)
Jenny V Lockard et al.
The journal of physical chemistry. A, 109(6), 1205-1215 (2006-07-13)
A quantitative model of mixed-valence excited-state spectroscopy is developed and applied to 2,3-diphenyl-2,3-diazabicyclo[2.2.2]octane. The lowest-energy excited state of this molecule arises from a transition from the ground state, where the charge is located on the hydrazine bridge, to an excited
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