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122-66-7 Usage

Description

Diphenylhydrazine is a man-made chemical that occurs in two isomeric forms: 1,1-diphenylhydrazine and 1,2-diphenylhdrazine. Diphenylhydrazine is produced by the reduction of nitrobenzene. Little or no information is available for 1,1-diphenylhydrazine. Most toxicological and use data pertain to 1,2-diphenylhydrazine.

Chemical Properties

yellow crystalline powder

Uses

Different sources of media describe the Uses of 122-66-7 differently. You can refer to the following data:
1. Impurity in the production of Phenylbutazone (P319570). Hydrazobenzene is a metabolic intermediate of Azobenzene Carcinogenic
2. Formerly used as a starting material in the production of benzidine for dyes; production of certain drugs.
3. Previously, 1,2-diphenylhydrazine was used for producing benzidine that was used in the synthesis of benzidine-based dyes. However, these dyes are no longer produced in the United States. The primary use of 1,2-diphenylhydrazine is in the production of the anti-inflammatory agent phenylbutazone and sulfinpyrazone, a uricosuric agent.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 36, p. 1529, 1988 DOI: 10.1248/cpb.36.1529Tetrahedron, 32, p. 2157, 1976 DOI: 10.1016/0040-4020(76)85128-9

General Description

Orange powder or a bright orange crystalline solid.

Air & Water Reactions

1,2-Diphenylhydrazine oxidizes in air. 1,2-Diphenylhydrazine decomposes in acid solutions. Insoluble in water.

Reactivity Profile

1,2-Diphenylhydrazine is a mild reducing agent. Incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides. Interaction with perchloryl fluoride in the presence of a dilutent below 32°F has caused separation of explosive solids. Is readily oxidized by nitric acid, silver nitrate or permanganate. Is reduced under alkaline conditions .

Health Hazard

1,2-Diphenylhydrazine is a liver toxin in rodents and appears to be carcinogenic in experimental animals.

Fire Hazard

Flash point data for 1,2-Diphenylhydrazine are not available; however, 1,2-Diphenylhydrazine is probably combustible.

Carcinogenicity

Hydrazobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental fate

Biological. When 5 and 10 mg/L of diphenylhydrazine was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, 80 and 72% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). Chemical/Physical. Wet oxidation of 1,2-diphenylhydrazine at 320 °C yielded formic and acetic acids (Randall and Knopp, 1980). 1,2-Diphenylhydrazine will not hydrolyze (Kollig, 1993). At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 16,000, 160, 1.5, and 0.015 mg/g, respectively (Dobbs and Cohen, 1980).

Purification Methods

Crystallise hydrazobenzene from hot EtOH containing a little ammonium sulfide or H2SO3 (to prevent atmospheric oxidation), preferably under N2. Dry it in a vacuum desiccator, and store it in the dark or under N2. Alternatively, crystallise it from pet ether (b 60-100o) to constant absorption spectrum. It is almost colourless but in air it turns yellow, then red with the formation of azobenzene. The hydrochloride crystallises from EtOH and has m 163-164o(dec); however, hydrazobenzene readily rearranges to benzidine in the presence of acid. The picrate crystallises from *C6H6 and has m 123o(dec). [Beilstein 15 H 123.]

Toxicity evaluation

The mechanism of action of diphenylhydrazine is not known. It is possible that some toxic effects may be attributed to its major metabolites, aniline and azobenzene, both of which are known carcinogens. Results of metabolism studies reporting aniline, benzidine, hyroxybenzidines, and aminophenols as metabolites in rats following multiple routes of administration suggest that the diphenylhydrazine metabolism may be similar to that of azobenzene and aniline. It is also possible that conversion of 1,2-diphenylhydrazine to aniline in the gastrointestinal tract may occur due to intestinal microflora and via acid hydrolysis.

Check Digit Verification of cas no

The CAS Registry Mumber 122-66-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 122-66:
(5*1)+(4*2)+(3*2)+(2*6)+(1*6)=37
37 % 10 = 7
So 122-66-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H

122-66-7 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A18037)  Hydrazobenzene, tech. 90%, remainder mainly azobenzene   

  • 122-66-7

  • 25g

  • 381.0CNY

  • Detail
  • Alfa Aesar

  • (A18037)  Hydrazobenzene, tech. 90%, remainder mainly azobenzene   

  • 122-66-7

  • 100g

  • 1170.0CNY

  • Detail
  • Supelco

  • (442232-U)  1,2-Diphenylhydrazine  analytical standard, ampule of 100 mg

  • 122-66-7

  • 442232-U

  • 620.10CNY

  • Detail
  • Aldrich

  • (126721)  Hydrazobenzene  

  • 122-66-7

  • 126721-25G

  • 409.50CNY

  • Detail

122-66-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-Diphenylhydrazine

1.2 Other means of identification

Product number -
Other names 1,2-Diphenyldiazane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Benzidines/Aromatic amines
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122-66-7 SDS

122-66-7Synthetic route

nitrobenzene
98-95-3

nitrobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
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

C24H22N4OSi2

diphenyl hydrazine
122-66-7

diphenyl hydrazine

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

Azobenzene

diphenyl hydrazine
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%
azoxybenzene
495-48-7

azoxybenzene

diphenyl hydrazine
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%
Azobenzene
1227476-15-4

Azobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

diphenyl hydrazine
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%
N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
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.
nitrobenzene
98-95-3

nitrobenzene

diphenyl hydrazine
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%
Azobenzene
1227476-15-4

Azobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
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%
Nitrosobenzene
586-96-9

Nitrosobenzene

diphenyl hydrazine
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
trans-azobenzene
17082-12-1

trans-azobenzene

diphenyl hydrazine
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%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With potassium hydroxide; platinum/charcoal In n-heptane; water; hydrogen91.5%
1,2-diphenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hydrazine

1,2-diphenyl-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hydrazine

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With water at 20℃; for 48h; Inert atmosphere;90%
With water at 20℃; for 0.166667h; Inert atmosphere;
1,2-bis(2-chlorophenyl)hydrazine
782-74-1

1,2-bis(2-chlorophenyl)hydrazine

butan-1-ol
71-36-3

butan-1-ol

A

2-Chloroaniline
95-51-2

2-Chloroaniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
A n/a
B 89.8%
azoxybenzene
495-48-7

azoxybenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Heating;A 6%
B 86%
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Product distribution; Heating;A 6%
B 86%
Azobenzene
1227476-15-4

Azobenzene

benzyl alcohol
100-51-6

benzyl alcohol

A

N-Benzylaniline
758640-21-0

N-Benzylaniline

B

benzylidene phenylamine
538-51-2

benzylidene phenylamine

C

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With 1 wtpercent of Pd on TiO2 In water at 29.84℃; for 4h; UV-irradiation; Inert atmosphere;A 85%
B 5%
C 10%
1-(dimethyl(phenyl)silyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hydrazine

1-(dimethyl(phenyl)silyl)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hydrazine

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With potassium tert-butylate In isopropyl alcohol; toluene at 20℃; for 22h; Inert atmosphere;85%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Azobenzene
1227476-15-4

Azobenzene

A

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;A 80%
B n/a
azoxybenzene
495-48-7

azoxybenzene

A

diphenyl hydrazine
122-66-7

diphenyl hydrazine

B

Azobenzene
1227476-15-4

Azobenzene

Conditions
ConditionsYield
With 1,3-bis(N',N'-dimethyl-4-aminopyridinium)propane diiodide; sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; UV-irradiation;A 5%
B 80%
With 1,3-bis(N',N'-dimethyl-4-aminopyridinium)propane diiodide; sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; UV-irradiation;A 73%
B 18%
With sulfur In various solvent(s) at 100℃; for 2h; in an autoclave;A 84 % Chromat.
B 12 % Chromat.
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With potassium hydroxide; aluminium In methanol at 20℃; for 0.416667h; Reduction; Reductive coupling;A 14%
B 80%
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

A

phenyltolylsulfone
640-57-3

phenyltolylsulfone

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 90℃;A 75%
B 12%
ethyl 2-diethoxyphosphorylpropionate
3699-66-9

ethyl 2-diethoxyphosphorylpropionate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Azobenzene
1227476-15-4

Azobenzene

A

ethyl (E)-3-(4-methoxyphenyl)-2-methylpropenoate
52750-05-7, 119870-81-4, 115754-00-2

ethyl (E)-3-(4-methoxyphenyl)-2-methylpropenoate

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;A 70%
B n/a
diethyl (dichloromethyl)phosphonate
3167-62-2

diethyl (dichloromethyl)phosphonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Azobenzene
1227476-15-4

Azobenzene

A

1-(2,2-dichlorovinyl)-4-methoxybenzene
41448-64-0

1-(2,2-dichlorovinyl)-4-methoxybenzene

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;A 70%
B n/a
nitrobenzene
98-95-3

nitrobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

C

Azobenzene
1227476-15-4

Azobenzene

D

azoxybenzene
495-48-7

azoxybenzene

Conditions
ConditionsYield
With indium; iodine In methanol at 50℃; for 12h; Product distribution; Further Variations:; reagents molar ratio;A 69%
B 20%
C n/a
D n/a

A

diphenyl hydrazine
122-66-7

diphenyl hydrazine

B

trans-azobenzene
17082-12-1

trans-azobenzene

Conditions
ConditionsYield
With 2-hydroxyethanethiol; {Fe(III)2Mn(II)O(OAc)6(Py)3} In N,N-dimethyl-formamide at 70℃; for 40h;A 66%
B 5%
nitrobenzene
98-95-3

nitrobenzene

A

diphenyl hydrazine
122-66-7

diphenyl hydrazine

B

Azobenzene
1227476-15-4

Azobenzene

Conditions
ConditionsYield
With indium(III) triflate; triethylsilane In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;A 29%
B 64%
With 1,3-bis(N',N'-dimethyl-4-aminopyridinium)propane diiodide; sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; UV-irradiation;A 59%
B 23%
With methanol; iodine; magnesium for 1h; Product distribution; Ambient temperature; other nitroarenes, var. time, var. molar ratio, var. alcohols, also oxygen;A 34.5 % Chromat.
B 65.4 % Chromat.
Nitrosobenzene
586-96-9

Nitrosobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Product distribution; Heating;A 16%
B 63%
With aluminum telluride; water In tetrahydrofuran for 0.333333h; Heating;A 16%
B 63%
O,O-diethyl benzylphosphonate
1080-32-6

O,O-diethyl benzylphosphonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Azobenzene
1227476-15-4

Azobenzene

A

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene
1694-19-5

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;A 60%
B n/a
O,O-diethyl benzylphosphonate
1080-32-6

O,O-diethyl benzylphosphonate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Azobenzene
1227476-15-4

Azobenzene

A

(E)-N,N-dimethyl-4-styrylbenzenamine
838-95-9

(E)-N,N-dimethyl-4-styrylbenzenamine

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; electrolysis;A 55%
B n/a
Azobenzene
1227476-15-4

Azobenzene

benzyl alcohol
100-51-6

benzyl alcohol

A

N-Benzylaniline
758640-21-0

N-Benzylaniline

B

benzylidene phenylamine
538-51-2

benzylidene phenylamine

C

aniline
62-53-3

aniline

D

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With 0.5 wtpercent of Pd on TiO2 In water at 29.84℃; for 4h; UV-irradiation; Inert atmosphere;A 47%
B 10%
C 10%
D 27%
With 2 wtpercent of Pd on TiO2 In water at 29.84℃; for 4h; UV-irradiation; Inert atmosphere;A 6%
B 24%
C 30%
D 30%
azoxybenzene
495-48-7

azoxybenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

C

Azobenzene
1227476-15-4

Azobenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol for 15h; Ambient temperature;A 17%
B 12.1%
C 45.7%
With sodium tetrahydroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In isopropyl alcohol at 82.4℃;
diphenyl hydrazine
122-66-7

diphenyl hydrazine

Azobenzene
1227476-15-4

Azobenzene

Conditions
ConditionsYield
With sodium periodate In dichloromethane at 20℃; for 1h;100%
With pyridine; bromine In dichloromethane at 0℃; for 0.25h;100%
With benzeneseleninic anhydride In tetrahydrofuran for 0.166667h; Ambient temperature;99%
diphenyl hydrazine
122-66-7

diphenyl hydrazine

trans-azobenzene
17082-12-1

trans-azobenzene

Conditions
ConditionsYield
With tert-butylhypochlorite; sodium iodide In acetonitrile at 20℃; for 1h; Inert atmosphere;100%
With potassium tert-butylate; ammonia at -75 - 20℃; for 0.05h; Reagent/catalyst; Temperature; Sealed tube;99%
With pyridine; oxygen; copper(I) bromide In toluene under 760.051 Torr; for 0.25h;98%
chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

diphenyl hydrazine
122-66-7

diphenyl hydrazine

C24H21N2P*2ClH

C24H21N2P*2ClH

Conditions
ConditionsYield
In dichloromethane at 20℃; for 48h;98%
dimethylbis(η5-pentamethylcyclopentadienyl)uranium
67605-92-9

dimethylbis(η5-pentamethylcyclopentadienyl)uranium

diphenyl hydrazine
122-66-7

diphenyl hydrazine

(C5Me5)2U(=NPh)2

(C5Me5)2U(=NPh)2

Conditions
ConditionsYield
With C6Me6 In diethyl ether (Ar or He); stirring (68 h); recrystn. (toluene/diethyl ether);98%
Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

diphenyl hydrazine
122-66-7

diphenyl hydrazine

N,N′,P,P-tetraphenylphosphinic hydrazide
64718-16-7

N,N′,P,P-tetraphenylphosphinic hydrazide

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 100℃; for 0.5h; Sealed tube;98%
4-Phenylbenzaldehyde
3218-36-8

4-Phenylbenzaldehyde

diphenyl hydrazine
122-66-7

diphenyl hydrazine

diethyl malonate
105-53-3

diethyl malonate

4-([1,1'-biphenyl]-4-yl)-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine-3,5-diol

4-([1,1'-biphenyl]-4-yl)-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine-3,5-diol

Conditions
ConditionsYield
With ammonium acetate In ethanol for 0.0333333h; Reflux; Green chemistry;98%
1,1'-thiocarbonylbis(1,2,4-triazole)
63976-76-1

1,1'-thiocarbonylbis(1,2,4-triazole)

diphenyl hydrazine
122-66-7

diphenyl hydrazine

[1,2,4]Triazole-1-carbothioic acid N,N'-diphenyl-hydrazide
90396-11-5

[1,2,4]Triazole-1-carbothioic acid N,N'-diphenyl-hydrazide

Conditions
ConditionsYield
In acetone for 1.5h; Heating;97%
diphenyl hydrazine
122-66-7

diphenyl hydrazine

methyl iodide
74-88-4

methyl iodide

N,N'-dimethyl-N,N'-diphenyl-hydrazine
14996-70-4

N,N'-dimethyl-N,N'-diphenyl-hydrazine

Conditions
ConditionsYield
Stage #1: diphenyl hydrazine; methyl iodide With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran; hexane for 3h; Further stages.;
97%
Stage #1: diphenyl hydrazine With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.25h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -60 - 20℃; for 4h; Inert atmosphere;
97%
tetrahydrofuran
109-99-9

tetrahydrofuran

diphenyl hydrazine
122-66-7

diphenyl hydrazine

C48H57Li3N6O3*C6H14

C48H57Li3N6O3*C6H14

Conditions
ConditionsYield
Stage #1: diphenyl hydrazine With trimethylsilylmethyllithium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
Stage #2: tetrahydrofuran In hexane at -20℃; Inert atmosphere;
97%
bis(4-methoxyphenyl)phosphine oxide
15754-51-5

bis(4-methoxyphenyl)phosphine oxide

diphenyl hydrazine
122-66-7

diphenyl hydrazine

P,P-bis(4-methoxyphenyl)-N,N′-diphenylphosphinic hydrazide

P,P-bis(4-methoxyphenyl)-N,N′-diphenylphosphinic hydrazide

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 100℃; for 1h; Sealed tube;97%
allyl bromide
106-95-6

allyl bromide

diphenyl hydrazine
122-66-7

diphenyl hydrazine

N-allyl-N,N'-diphenylhydrazine
40395-35-5

N-allyl-N,N'-diphenylhydrazine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 1h;96%
Stage #1: diphenyl hydrazine With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.25h; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Inert atmosphere;
96%
With tetra(n-butyl)ammonium hydroxide; potassium bromide In dichloromethane
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

diphenyl hydrazine
122-66-7

diphenyl hydrazine

4-(4-bromophenyl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

4-(4-bromophenyl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

Conditions
ConditionsYield
With ammonium acetate In ethanol for 0.5h; Reflux; Green chemistry;96%
Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

diphenyl hydrazine
122-66-7

diphenyl hydrazine

ethyl 2-(1,2-diphenylhydrazino)-2-oxoacetate
97738-62-0

ethyl 2-(1,2-diphenylhydrazino)-2-oxoacetate

Conditions
ConditionsYield
With triethylamine95%
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

diphenyl hydrazine
122-66-7

diphenyl hydrazine

4-(1H-indol-3-yl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

4-(1H-indol-3-yl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

Conditions
ConditionsYield
With ammonium acetate In ethanol for 0.5h; Reflux; Green chemistry;95%
diphenyl hydrazine
122-66-7

diphenyl hydrazine

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 12h;93%
With titanium tetrachloride; magnesium In tetrahydrofuran at 20℃; Inert atmosphere;91%
With β-D-glucose; water at 25℃; for 10h; UV-irradiation;90%
dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

diphenyl hydrazine
122-66-7

diphenyl hydrazine

A

N-phenyl-N',N-dicyclohexylguanidine
4833-42-5

N-phenyl-N',N-dicyclohexylguanidine

B

trans-azobenzene
17082-12-1

trans-azobenzene

Conditions
ConditionsYield
With trimethylsilylmethyllithium In benzene at 110℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;A 93%
B n/a
(4-methoxyphenyl)(phenyl)phosphine oxide

(4-methoxyphenyl)(phenyl)phosphine oxide

diphenyl hydrazine
122-66-7

diphenyl hydrazine

P-(4-methoxyphenyl)-N,N′,P-triphenylphosphinic hydrazide

P-(4-methoxyphenyl)-N,N′,P-triphenylphosphinic hydrazide

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 100℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Sealed tube;93%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-Phenylbenzaldehyde
3218-36-8

4-Phenylbenzaldehyde

diphenyl hydrazine
122-66-7

diphenyl hydrazine

4-([1,1'-biphenyl]-4-yl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

4-([1,1'-biphenyl]-4-yl)-3,5-dimethyl-1,7-diphenyl-1,4,7,8-tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridine

Conditions
ConditionsYield
With ammonium acetate In ethanol for 0.5h; Reflux; Green chemistry;93%
phenylborondichloride
873-51-8

phenylborondichloride

diphenyl hydrazine
122-66-7

diphenyl hydrazine

hexaphenyl-1.2.4.5-tetraaza-3.6-diborane
13831-68-0

hexaphenyl-1.2.4.5-tetraaza-3.6-diborane

Conditions
ConditionsYield
With triethylamine In benzene 4 h heating 40-60°C;92%
With (C2H5)3N In benzene 4 h heating 40-60°C;92%
With triethylamine In benzene
2-(p-methoxyphenyl)-4-phenyl-6-(p-nitrophenyl)-3,4-dihydro-2H-sym-tetrazin-1-yl
99910-01-7

2-(p-methoxyphenyl)-4-phenyl-6-(p-nitrophenyl)-3,4-dihydro-2H-sym-tetrazin-1-yl

diphenyl hydrazine
122-66-7

diphenyl hydrazine

A

2-(p-methoxyphenyl)-4-phenyl-6-(p-nitrophenyl)-1,2,3,4-tetrahydro-sym-tetrazine
96385-57-8

2-(p-methoxyphenyl)-4-phenyl-6-(p-nitrophenyl)-1,2,3,4-tetrahydro-sym-tetrazine

B

Azobenzene
1227476-15-4

Azobenzene

Conditions
ConditionsYield
In benzeneA 92%
B 90%
In acetonitrile at 20℃; Rate constant; Equilibrium constant; activation energy (Ea), ΔS(excit.);

122-66-7Related news

Reactions of W2(H)(OR)7, W2(OR)6(py)2 and W4(OCH2cC4H7)12 compounds (R = Pri, CH2But, cC5H9) with azobenzene, 1,2-Diphenylhydrazine (cas 122-66-7) and 1,1-dimethylhydrazine09/09/2019

The reaction of W2(H)(OR)7, W2(OR)6(py)2 and W4(OCH2cC4H7)12 compounds (R = Pri, CH2But, cC5H9) in hydrocarbon solvents with azobenzene, 1,2-diphenylhydrazine and 1,1-dimethylhydrazine have been studied. The tetranuclear cluster proved to be inert while W2(H)(OR)7 was the most kinetically labile...detailed

ArticlesKinetics and mechanism of the oxidative dehydrogenation of 1,2-Diphenylhydrazine (cas 122-66-7) with molecular O2 catalyzed by triphenylphosphinecobaloxime(II)09/08/2019

1,2-Diphenylhydrazine (H2AB) is catalytically oxidized to azobenzene (AB) in the presence of triphenylphosphinecobaloxime(II), Cox, at 1 bar O2 and 30 °C. The catalytic reaction does not involve H2O2 as intermediate or product, and its rate is independent of the O2-pressure. The rate law is of ...detailed

122-66-7Relevant articles and documents

Highly efficient and selective photocatalytic hydrogenation of functionalized nitrobenzenes

Yang, Xiu-Jie,Chen, Bin,Zheng, Li-Qiang,Wu, Li-Zhu,Tung, Chen-Ho

, p. 1082 - 1086 (2014)

We report a simple but efficient photocatalytic nitrobenzene reduction method employing eosin Y as the photocatalyst and TEOA as the reducing agent. With green LED light irradiation, the nitro group in the nitrobenzenes containing other reducible groups was chemoselectively reduced into an amino group, and the corresponding anilines were isolated in quantitative yields. The photoinduced electron transfer mechanism suggests that the high chemoselectivity originates from the better electron-withdrawing ability of the nitro group.

Catalytic Hydrogenation of Azobenzene in the Presence of a Cuboidal Mo3S4Cluster via an Uncommon Sulfur-Based H2Activation Mechanism

Guillamón, Eva,Oliva, Mónica,Andrés, Juan,Llusar, Rosa,Pedrajas, Elena,Safont, Vicent S.,Algarra, Andres G.,Basallote, Manuel G.

, p. 608 - 614 (2021)

Azobenzene hydrogenation is catalyzed under moderate conditions by a cuboidal Mo3(μ3-S)(μ-S)3 diamino complex via a cluster catalysis mechanism. Dihydrogen activation by the molecular [Mo3(μ3-S)(μ-S)3Cl3(dmen)3]+ cluster cation takes place at the μ-S bridging atoms without direct participation of the metals in clear contrast with classical concepts. The reaction occurs with the formation of 1,2-diphenylhydrazine as an intermediate with similar appearance and disappearance rate constants. On the basis of DFT calculations, a mechanism is proposed in which formation of 1,2-diphenylhydrazine and aniline occurs through two interconnected catalytic cycles that share a common reaction step that involves H2 addition to two of the bridging sulfur atoms of the catalyst to form a dithiolate Mo3(μ3-S)(μ-SH)2)(μ-S) adduct. Both catalytic cycles have similar activation barriers, in agreement with the experimental observation of close rate constant values. Microkinetic modeling of the process leads to computed concentration-time profiles in excellent agreement with the experimental ones providing additional support to the calculated reaction mechanism. Slight modifications on the experimental conditions of the catalytic protocol in combination with theoretical calculations discard a direct participation of the metal on the reaction mechanism. The effect of the ancillary ligands on the catalytic activity of the cluster fully agrees with the present mechanistic proposal. The results herein demonstrate the capability of molybdenum sulfide materials to activate hydrogen through an uncommon sulfur based mechanism opening attractive possibilities toward their applications as catalysts in other hydrogenation processes.

-

Urey,Lavin

, p. 3288 (1929)

-

Newsom, H. C.,English, W. D.,McCloskey, A. L.,Woods, W. G.

, p. 4134 - 4138 (1961)

μ-imido, μ-(η2,η2-N,N-hydrazido) and μ-(η1-C:η2-C,N-isocyanido) dinuclear (fulvalene)zirconium derivatives

Gonzalez-Maupoey, Marta,Rodriguez, Gema M.,Cuenca, Tomas

, p. 2057 - 2063 (2002)

Treatment of the chloro (fulvalene)zirconium(III) compound [Zr(η5-C5H5)(μ-Cl)]2 [μ-(η5,η5-C10H8)] with an equimolar amount of azobenzene in toluene, under extremely anhydrous conditions, gives the μ-[bis(imido)] derivative [Zr(η5- C5H5)(μ-NPh)]2[μ-(η5, η5-C10H8)] (1). However, when this reaction is carried out under insufficiently dry conditions a mixture of the previously reported μ-oxo complex [Zr(η5- C5H5)Cl]2(μ-O)[μ-(η5, η5-C10H8)] and 1,2-diphenylhydrazine is obtained. When the chloro(fulvalene)zirconium(III) compound reacts with benzo[c]cinnoline the μ-(η2,η2-N,N-hydrazido) complex [Zr(η5-C5H5)Cl]2[μ- (NC6H4C6H4N)][μ (η5,η5-C10H8)] (2a) is obtained, which rearranges to the thermodynamically more stable 2b. Addition of an equimolar amount of RNC (R = nBu, C6H11) to a toluene solution of [Zr(η5-C5H5)(μ-Cl)]2 [μ-(η5,η5-C10H8)] gives [Zr(η5- C5H5)Cl]2(μ-CNR)[μ- (η5,η5-C10H8)] [R = nBu (3), C6H11 (4)]. Reaction of [Zr(η5-C5H5)Cl]2(μ-CNtBu) [μ-(η5,η5-C10H8)] with 1 equiv, of PhCH2MgCl or (PhCH2)2Mg(THF)2 afforded the monobenzyl derivatives [Zr(η5-C5H5)]2 (CH2Ph)(Cl)(μ-CNtBu) [μ-(η5,η5-C10H8)] (5 and 6). When this reaction was carried out with 2 equiv. or an excess of PhCH2MgCl, a mixture of the monobenzyl and dibenzyl compounds [Zr(η5- C5H5)]2(CH2Ph)(Cl) (μ-CNtBu)[μ-(η5,η5- C10H8)] (5) and [Zr(η5-C5H5) (CH2Ph)]2(μ-CNtBu)[μ-(η5, η5-C10H8)] (7) is obtained. Similar reactions with 1 or 2 equiv. of (CH3)3SiCH2Li afford a mixture of the monoalkyl and dialkyl compounds [Zr(η5-C5H5)]2 [CH2Si(CH3)3](Cl)(μ-CNtBu) [μ-(η5,η5-C10H8)] (8) and {Zr(η5-C5H5)[CH2Si (CH3)3]}2(μ-CNtBu) [μ-(η5,η5- C10H8)] (9) compounds. Moreover, methylation of [Zr(η5- C5H5)Cl]2(μ-CNnBu) [μ-(η5,η5-C10H8)] gives the analytically pure tetramethyl derivative [Zr(η5-C5H5) (CH3)]2(μ-CNnBu) [μ-(η5,η5-C10H8)] (10), whereas [Zr(η5-C5H5)Cl]2(μ- CNC6H11)[μ-(η5, μ5-C10H8)] reacts with MeLi to give a mixture of the monomethyl derivatives [Zr(η5C5H5)]2 (CH3)(Cl)(μ-CNC6H11)[μ- (η5,η5-C10H8)] (11 and 12), as well as the dimethyl compound [Zr(η5-C5H5) (CH3)]2(μ- CNC6H11)[μ-(η5, η5-C10H8)] (13). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

N=N bond cleavage of azobenzene through Pt/TiO2 photocatalytic reduction

Tada, Hiroaki,Kubo, Masanobu,Inubushi, Yoichi,Ito, Seishiro

, p. 977 - 978 (2000)

TiO2 photocatalytic 2e--reduction of azobenzene to hydrazobenzene is found to occur at λ(ex) > 300 nm while loading of nanometer-sized Pt particles on TiO2 induces N=N bond cleavage via 4e--reduction; only photoisomerization occurs in the absence of TiO2.

-

Banthorpe et al.

, p. 2054 (1971)

-

-

Shine et al.

, p. 3719,3721,3722 (1977)

-

-

Hashimoto,S.,Kano,K.

, p. 852 - 855 (1972)

-

-

Wawzonek

, p. 285,290 (1971)

-

Reduction of Azo-, Azoxy-, and Nitrobenzenes by Dihydrolipoamide-Iron(II)

Kijima, Masashi,Nambu, Yoko,Endo, Takeshi,Okawara, Makoto

, p. 2407 - 2409 (1983)

Dihydrolipoamide (DHLAm) was found to be an effective reagent for the reduction of nitrobenzene derivatives in the presence of a catalytic amount of ferrous ion.Azo- and azoxybenzenes were reduced to hydrazobenzene without the formation of aniline, and nitrobenzene, nitrosobenzene, and phenylhydroxylamine were also reduced to aniline in good yields under mild conditions.The reduction was presumed to proceed through the complex formation between DHLAm, ferrous ion, and substrates.

-

Pratt,Swinden

, p. 1321 (1969)

-

Synthesis of Functionalized Hydrazines: Facile Homogeneous (N-Heterocyclic Carbene)-Palladium(0)-Catalyzed Diboration and Silaboration of Azobenzenes

Ansell, Melvyn B.,Kostakis, George E.,Braunschweig, Holger,Navarro, Oscar,Spencer, John

, p. 3765 - 3769 (2016)

The bis(N-heterocyclic carbene)(diphenylacetylene)palladium complex [Pd(ITMe)2(PhC≡CPh)] (ITMe=1,3,4,5-tetramethylimidazol-2-ylidene) acts as a highly active pre-catalyst in the diboration and silaboration of azobenzenes to synthesize a series of novel functionalized hydrazines. The reactions proceed using commercially available diboranes and silaboranes under mild reaction conditions. (Figure presented.).

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Chang, Liu,Li, Jin,Wu, Na,Cheng, Xu

supporting information, p. 2468 - 2472 (2021/04/02)

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Visible-light-promoted decarboxylative addition cyclization of: N -aryl glycines and azobenzenes to access 1,2,4-triazolidines

Ma, Ben,Qi, Yanfang,Song, Menghui,Wang, Xi-Cun,Yang, Jingya,Zhou, Hongyan

, p. 5806 - 5811 (2021/08/23)

Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N-aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the reaction proceeded smoothly in the absence of transition-metal catalysts at ambient temperature, affording the corresponding products, 1,2,4-triaryl 1,2,4-triazolidines, in good to excellent yields. This work demonstrates a new synthetic application of readily available azobenenes and provides a novel strategy for constructing 1,2,4-triazolidines.

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