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126721

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:
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

Signal Word

Danger

Hazard Statements

H302,H350,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK3454
BCCH6855
BCCF3480
BCCC6359
BCCB1611

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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.
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
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)
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