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122-66-7

Basic Information
CAS No.: 122-66-7
Name: 1,2-Diphenylhydrazine
Article Data: 310
Molecular Structure:
Molecular Structure of 122-66-7 (1,2-Diphenylhydrazine)
Formula: C12H12N2
Molecular Weight: 184.241
Synonyms: Hydrazobenzene(8CI);Benzene,1,1'-hydrazobis-;N,N'-Bianiline;N,N'-Diphenylhydrazine;
EINECS: 204-563-5
Density: 1.179 g/cm3
Melting Point: 123-126 °C(lit.)
Boiling Point: 229.3 °C at 760 mmHg
Flash Point: 87.7 °C
Solubility: 221 mg/L at 25 °C (U.S. EPA, 1980a)
Appearance: yellow crystalline powder
Hazard Symbols: ToxicT, DangerousN
Risk Codes: 45-22-50/53
Safety: 53-45-60-61
Transport Information: UN 3077 9/PG 3
PSA: 24.06000
LogP: 3.27160
Synthetic route
98-95-3

nitrobenzene

A

62-53-3

aniline

B

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With ammonia borane; gold on titanium oxide In ethanol at 20℃; for 0.5h; Inert atmosphere;A 92%
B 100%
With samarium; iodine; ammonium chloride In tetrahydrofuran; water at 20℃; for 4h; Reduction;A 56%
B 20%
Electrolysis;

C24H22N4OSi2

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In chloroform-d1; water at 20℃; for 0.0833333h;100%
1227476-15-4

Azobenzene

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With borane-ammonia complex; [C6H3-2,6-(CHN(t-Bu))2]Bi; water In tetrahydrofuran at 35℃; for 2h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;99%
With ammonium formate; 1-butyl-3-methylimidazolium Tetrafluoroborate; zinc In water at 20℃; for 0.416667h;98%
With hydrogen; potassium hydroxide In para-xylene at 80℃; for 5h;98.1%
495-48-7

azoxybenzene

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With sodium hydrogensulfide In ammonia at 40℃; for 5h; Product distribution;99%
With hydrazine hydrate; sodium hydroxide; [1,4]naphthoquinone at 55℃; for 6h; Temperature;99%
With sodium dithionite; 1,1′-dioctyl-4,4′-bipyridinium; potassium carbonate In water; acetonitrile at 35℃; for 1h;96%
1227476-15-4

Azobenzene

73183-34-3

bis(pinacol)diborane

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
Stage #1: Azobenzene; bis(pinacol)diborane With pyridine-4-carbonitrile In pentane at 70℃; for 24h; Inert atmosphere;
Stage #2: With water In pentane at 20℃; for 0.25h; Concentration; Temperature;
99%
100-65-2

N-Phenylhydroxylamine

A

62-53-3

aniline

B

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Product distribution; Heating;A 98%
B 1%
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Heating;A 98%
B 1%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,10-Phenanthroline; isopropyl alcohol; potassium hydroxide at 83℃; for 2h; Schlenk technique; Inert atmosphere;A 89 %Chromat.
B 11 %Chromat.
98-95-3

nitrobenzene

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With triethylsilane; indium(III) bromide In N,N-dimethyl-formamide at 60℃; for 8h;96%
With ammonia; lithium perchlorate In acetonitrile at 20℃; Electrolysis; chemoselective reaction;96%
With potassium hydroxide; aluminium In methanol at 20℃; for 0.25h; Reduction; Reductive coupling;95%
1227476-15-4

Azobenzene

A

62-53-3

aniline

B

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Heating;A 4%
B 96%
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Product distribution; Heating;A 4%
B 96%
With lithium vanadium(I) dihydride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;A 15%
B 85%
586-96-9

Nitrosobenzene

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With triethylsilane; indium(III) bromide In N,N-dimethyl-formamide at 60℃;94%
With diethyl ether; magnesium; magnesium iodide weiteres Reagens: Benzol; Eintragen des Reaktionsgemisches in Wasser;
Multi-step reaction with 3 steps
1: hydrazine
2: ; oxygen / ethanol / 1 h / 60 °C
3: ; hydrazine / 20 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: acetic acid / ethanol / 20 °C / Inert atmosphere
2: potassium carbonate; C30H29BrMnNO2P2; hydrogen / toluene / 24 h / 135 °C / 60006 Torr / Glovebox; Autoclave
View Scheme
17082-12-1

trans-azobenzene

122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 60℃; for 0.5h;92%
With borane-ammonia complex; tris(quinolin-8-yl)phosphite In tetrahydrofuran at 60℃; Kinetics; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; Sealed tube;91%
With sodium hydrogencarbonate; hydrazine hydrate; zirconium(IV) oxide In ethanol; water for 10h; Heating;86%
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Consensus Reports

NTP 10th Report on Carcinogens. NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-92 ,1978. . Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

Specification

The Hydrazobenzene with CAS registry number of 122-66-7 is also called Hydrazine,1,2-diphenyl-. The IUPAC name is 1,2-diphenylhydrazine. Its EINECS registry number is 204-563-5. In addition, the molecular formula is C12H12N2 and the molecular weight is 184.24. It is a kind of yellow crystalline powder.

Physical properties about this chemical are: (1)ACD/LogP: 2.94; (2)ACD/LogD (pH 5.5): 2.94; (3)ACD/LogD (pH 7.4): 2.94; (4)ACD/BCF (pH 5.5): 100.69; (5)ACD/BCF (pH 7.4): 101.01; (6)ACD/KOC (pH 5.5): 943.92; (7)ACD/KOC (pH 7.4): 946.98; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 6.48 Å2; (12)Index of Refraction: 1.7; (13)Molar Refractivity: 60.4 cm3; (14)Molar Volume: 156.2 cm3; (15)Polarizability: 23.94 ×10-24cm3; (16)Surface Tension: 52.5 dyne/cm; (17)Density: 1.179 g/cm3; (18)Flash Point: 87.7 °C; (19)Enthalpy of Vaporization: 46.59 kJ/mol; (20)Boiling Point: 229.3 °C at 760 mmHg; (21)Vapour Pressure: 0.07 mmHg at 25°C.

Preparation of Hydrazobenzene: it can be prepared by diphenyldiazene. This reaction is a kind of reduction reaction. And it will need reagents ultrasonically activated nickel and N2H4*H2O, and solvents toluene and tetrahydrofuran. The reaction time is 5 minutes at reaction temperature of 20 °C. The yield is about 90.3%.

Hydrazobenzene can be prepared by diphenyldiazene

Uses of Hydrazobenzene: this chemical can be used to produce anti-inflammatory drugs in pharmaceutical industry and benzidine dyes. In addition, it can be used to get trans-diphenyldiazene and aniline. This reaction will need reagent hydrated HZSM-5. The reaction time is 30 minutes at reaction temperature of 150 °C. The yield is about 59%.

Hydrazobenzene can be used to get trans-diphenyldiazene and aniline

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and may cause cancer. In addition, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. You should avoid exposure-obtain special instructions before use. During using it, you should avoid release to the environment. And you can refer to special instructions/safety data sheets. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: c2(NNc1ccccc1)ccccc2
(2)InChI: InChI=1/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H
(3)InChIKey: YBQZXXMEJHZYMB-UHFFFAOYAR