Product Name

  • Name

    N,N'-Diphenylbenzidine

  • EINECS 208-521-7
  • CAS No. 531-91-9
  • Article Data39
  • CAS DataBase
  • Density 1.173 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 246-248 °C(lit.)
  • Formula C24H20N2
  • Boiling Point 535 °C at 760 mmHg
  • Molecular Weight 336.436
  • Flash Point 342 °C
  • Transport Information UN 2811
  • Appearance grey to brownish fine crystalline powder
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 531-91-9 (N,N'-Diphenylbenzidine)
  • Hazard Symbols IrritantXi
  • Synonyms Benzidine,N,N'-diphenyl- (6CI,7CI,8CI);[1,1'-Biphenyl]-4,4'-diamine, N,N'-diphenyl-(9CI);4,4'-Bis(phenylamino)-1,1'-biphenyl;4,4'-Bis(phenylamino)biphenyl;N,N'-Diphenyl-[1,1'-biphenyl]-4,4'-diamine;N,N'-Diphenyl-p,p'-biphenylenediamine;[1,1'-Biphenyl]-4,4'-diamine,N4,N4'-diphenyl-;
  • PSA 24.06000
  • LogP 6.98680

Synthetic route

chlorobenzene
108-90-7

chlorobenzene

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;95%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium hydroxide In tetrahydrofuran; ethanol; water; toluene; tert-butyl alcohol at 100℃; for 16h; Glovebox; Inert atmosphere; Schlenk technique;116.5 mg
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

aniline
62-53-3

aniline

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Stage #1: 4-(4-bromophenyl)bromobenzene; aniline In 1-methyl-pyrrolidin-2-one; toluene at 20℃; for 0.25h;
Stage #2: With sodium t-butanolate In 1-methyl-pyrrolidin-2-one; toluene for 0.166667h;
Stage #3: tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1-methyl-pyrrolidin-2-one; toluene at 20 - 60℃; for 24.5h; Product distribution / selectivity;
93.1%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 90℃; for 3h;90%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 3h;90%
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

N-trimethylsilylaniline
3768-55-6

N-trimethylsilylaniline

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Stage #1: N-trimethylsilylaniline With n-butyl magnesium bromide In dibutyl ether at 0 - 100℃; for 1h; Inert atmosphere;
Stage #2: 4-(4-bromophenyl)bromobenzene With lithium bromide; iron(II) chloride In dibutyl ether at 140℃; for 24h; Inert atmosphere;
87%
bromobenzene
108-86-1

bromobenzene

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux;80.2%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Reflux;46.1 g
diphenylamine
122-39-4

diphenylamine

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Stage #1: diphenylamine With methanesulfonic acid In dichloromethane at 0℃;
Stage #2: With chloranil In dichloromethane at 0 - 20℃; for 24h;
38%
With aluminum (III) chloride In neat (no solvent) at 95℃; Reagent/catalyst; Temperature;14.9%
With pyridine; nitrosonium tetrafluoroborate In acetonitrile Mechanism;
tetraphenylhydrazine
632-52-0

tetraphenylhydrazine

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With sulfuric acid; acetic acid
With sulfuric acid
With hydrogenchloride
N,N-diphenylhydroxylamine
1079-64-7

N,N-diphenylhydroxylamine

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With sulfuric acid at -20℃;
N,N'-biphenyl-4,4'-diyl-di-anthranilic acid
53036-42-3

N,N'-biphenyl-4,4'-diyl-di-anthranilic acid

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
at 285℃;
at 285℃;
N,N'-dinitroso-N,N'-diphenyl-benzidine
40317-17-7

N,N'-dinitroso-N,N'-diphenyl-benzidine

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With sulfuric acid; acetic acid Reduktion der entstandenen Loesung mit Zinkstaub;
tetrachloromethane
56-23-5

tetrachloromethane

1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane

1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1,1-Diphenylhydrazine
530-50-7

1,1-Diphenylhydrazine

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

N-phenyl-1,2-benzenediamine
534-85-0

N-phenyl-1,2-benzenediamine

Conditions
ConditionsYield
With sulfuric acid at -16℃;
acetic acid
64-19-7

acetic acid

1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane

1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane

zinc

zinc

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

sulfuric acid
7664-93-9

sulfuric acid

diphenylamine
122-39-4

diphenylamine

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
elektrolytische Oxydation und Reduktion des entstandenen kristallinischen Produkts mit Zink;
sulfuric acid
7664-93-9

sulfuric acid

diphenylamine
122-39-4

diphenylamine

sodium dichromate

sodium dichromate

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
bei der Reduktion des entstandenen blauen Produkts mit NaHSO3 oder Zinkstaub;
sulfuric acid
7664-93-9

sulfuric acid

diphenylamine
122-39-4

diphenylamine

sodium nitrite

sodium nitrite

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

N,N'-dinitroso-N,N'-diphenyl-benzidine
40317-17-7

N,N'-dinitroso-N,N'-diphenyl-benzidine

C

N,N'-bis-(4-nitroso-phenyl)-benzidine
88855-71-4

N,N'-bis-(4-nitroso-phenyl)-benzidine

Conditions
ConditionsYield
bei folgendem Zusatz von Eis zum Reaktionsgemisch;
sulfuric acid
7664-93-9

sulfuric acid

sulfur trioxide
7446-11-9

sulfur trioxide

diphenylamine
122-39-4

diphenylamine

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

N.N'-diphenyl-benzidine sulfone

N.N'-diphenyl-benzidine sulfone

Conditions
ConditionsYield
at 80℃;
at 80℃;
sulfuric acid
7664-93-9

sulfuric acid

1,1-Diphenylhydrazine
530-50-7

1,1-Diphenylhydrazine

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

4-anilinophenol
122-37-2

4-anilinophenol

C

N-phenyl-1,2-benzenediamine
534-85-0

N-phenyl-1,2-benzenediamine

Conditions
ConditionsYield
at -16℃; anschl. Erwaermen auf 20grad;
sulfuric acid
7664-93-9

sulfuric acid

tetraphenylhydrazine
632-52-0

tetraphenylhydrazine

acetic acid
64-19-7

acetic acid

benzene
71-43-2

benzene

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
nachf. Reduktion mit Zinkstaub;
tetraphenylhydrazine
632-52-0

tetraphenylhydrazine

benzene
71-43-2

benzene

etheric hydrochloric acid

etheric hydrochloric acid

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

N-(4-chloro-phenyl)-N',N'-diphenyl-p-phenylenediamine
857468-42-9

N-(4-chloro-phenyl)-N',N'-diphenyl-p-phenylenediamine

C

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
in Kohlendioxyd-Atmosphaere;
sulfuric acid
7664-93-9

sulfuric acid

N,N-diphenylhydroxylamine
1079-64-7

N,N-diphenylhydroxylamine

A

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
at -20℃;
sulfuric acid
7664-93-9

sulfuric acid

N,N'-dinitroso-N,N'-diphenyl-benzidine
40317-17-7

N,N'-dinitroso-N,N'-diphenyl-benzidine

acetic acid
64-19-7

acetic acid

zinc

zinc

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

N-nitrosodiphenylamine
382165-80-2

N-nitrosodiphenylamine

A

tetraphenylhydrazine
632-52-0

tetraphenylhydrazine

B

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With HY zeolite In dichloromethane at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;
p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; copper; amyl alcohol
2: 285 °C
View Scheme
ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; copper; amyl alcohol
2: 285 °C
View Scheme
diphenylamine
122-39-4

diphenylamine

A

p,p'-(N,N'-diphenyl)diaminobis(phenyl)amine

p,p'-(N,N'-diphenyl)diaminobis(phenyl)amine

B

tetraphenylhydrazine
632-52-0

tetraphenylhydrazine

C

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Electrolysis;
aniline
62-53-3

aniline

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / cyclohexane / 2 h / 5 °C / Inert atmosphere
1.2: 18 h / 5 °C / Inert atmosphere
2.1: n-butyl magnesium bromide / dibutyl ether / 1 h / 0 - 100 °C / Inert atmosphere
2.2: 24 h / 140 °C / Inert atmosphere
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium acetate; tetrahydroxydiboron; dicyclohexyl(2',4',6'-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane; Pd(Cy*Phine)2Cl2 / tert-butyl alcohol; ethanol / 80 °C / Glovebox; Inert atmosphere; Schlenk technique; Sealed tube
1.2: 3.5 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique
2.1: sodium hydroxide; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene; tetrahydrofuran; tert-butyl alcohol; ethanol; water / 16 h / 100 °C / Glovebox; Inert atmosphere; Schlenk technique
View Scheme
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1-bromo-3-(2-(2-methoxyethoxy)ethoxy)benzene

1-bromo-3-(2-(2-methoxyethoxy)ethoxy)benzene

C46H48N2O6

C46H48N2O6

Conditions
ConditionsYield
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux;100%
1-bromo-3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene
318261-63-1

1-bromo-3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C50H56N2O8

C50H56N2O8

Conditions
ConditionsYield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 3h; Inert atmosphere; Reflux;100%
9-chloro-11,11-dimethylbenzo[a]fluorene
954137-80-5

9-chloro-11,11-dimethylbenzo[a]fluorene

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C62H48N2
954137-37-2

C62H48N2

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In xylene at 125℃; for 15h;99%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1-bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene
125808-05-1

1-bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene

C50H56N2O8

C50H56N2O8

Conditions
ConditionsYield
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux;99%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
2620-76-0

2-(4-bromophenyl)-1-phenyl-1H-benzimidazole

N,N'-diphenyl-N,N'-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine
1416621-06-1

N,N'-diphenyl-N,N'-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; xylene at 130℃; for 4.5h; Hartwig-Buchwald reaction; Inert atmosphere;96%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl

4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 20 - 130℃; Inert atmosphere;95%
With tri-tert-butyl phosphine; sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;70%
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate; palladium diacetate In toluene for 72h; Heating;54%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]-1,1'-biphenyl

4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]-1,1'-biphenyl

Conditions
ConditionsYield
With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 80℃; for 6h;93%
With sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 80℃; for 6h;93%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

N',N"-bis[4-(diphenylamino)phenyl]-N',N"-diphenyl biphenyl-4,4'-diamine
209980-53-0

N',N"-bis[4-(diphenylamino)phenyl]-N',N"-diphenyl biphenyl-4,4'-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 50℃; for 7h; Inert atmosphere;91%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1,6-bis(4-iodophenoxy)hexane

1,6-bis(4-iodophenoxy)hexane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxyhexamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,6-bis(4-iodophenoxy)hexane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxyhexamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,6-bis(4-iodophenoxy)hexane

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 72h; Ullmann reaction; Heating;90%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1,12-bis(4-iodophenoxy)dodecane

1,12-bis(4-iodophenoxy)dodecane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxydodecamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,12-bis(4-iodophenoxy)dodecane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxydodecamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,12-bis(4-iodophenoxy)dodecane

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene Ullmann reaction; Heating;90%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

N,N′-diphenyl-3-(phenylsulfonyl)-[1,1′-biphenyl]-4,4′-diamine

N,N′-diphenyl-3-(phenylsulfonyl)-[1,1′-biphenyl]-4,4′-diamine

Conditions
ConditionsYield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;90%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

N,N′-diphenyl-3-tosyl-[1,1′-biphenyl]-4,4′-diamine

N,N′-diphenyl-3-tosyl-[1,1′-biphenyl]-4,4′-diamine

Conditions
ConditionsYield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;90%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C48H36N4

C48H36N4

Conditions
ConditionsYield
In perchloric acid; water; N,N-dimethyl-formamide Electrolysis;90%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C11H7BrN2O2

C11H7BrN2O2

C46H32N6O4

C46H32N6O4

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; (1R,2R)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;88%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1,10-bis(4-iodophenoxy)decane

1,10-bis(4-iodophenoxy)decane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxydecamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,10-bis(4-iodophenoxy)decane

poly[1,4-phenylene(phenylimino)biphenyl-4,4-ylene(phenylimino)-1,4-phenyleneoxydecamethyleneoxy]; Monomer(s): N,N-diphenylbenzidine; 1,10-bis(4-iodophenoxy)decane

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene Ullmann reaction; Heating;87.5%
3-bromo-9-ethyl-9H-carbazole
57102-97-3

3-bromo-9-ethyl-9H-carbazole

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C52H42N4

C52H42N4

Conditions
ConditionsYield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 50℃; for 6.5h; Inert atmosphere;87%
4-tolyl iodide
624-31-7

4-tolyl iodide

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine
20441-06-9

N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 190℃; for 14h; Ullmann condensation;86%
C12H14BrN

C12H14BrN

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C48H46N4

C48H46N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 8h; Inert atmosphere;86%
1-iodo-2,4-dimethylbenzene
4214-28-2

1-iodo-2,4-dimethylbenzene

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine
122738-25-4

N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 20 - 190℃; Inert atmosphere;85%
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 170℃; for 48h;50%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

1-bromo-4-(trifluorovinyloxy)benzene

1-bromo-4-(trifluorovinyloxy)benzene

N,N'-bis[(p-trifluorovinyloxy)phenyl]-N,N'-bis(phenyl)benzidine
1159606-87-7

N,N'-bis[(p-trifluorovinyloxy)phenyl]-N,N'-bis(phenyl)benzidine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Reflux; Inert atmosphere;85%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-[(4-chlorophenyl)sulfonyl]-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine

3-[(4-chlorophenyl)sulfonyl]-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine

Conditions
ConditionsYield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;85%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

polymer; monomer(s): N-methyl-3,4-bis-(4-bromophenyl)maleimide; N,N\-diphenylbenzidine

polymer; monomer(s): N-methyl-3,4-bis-(4-bromophenyl)maleimide; N,N\-diphenylbenzidine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In tetrahydrofuran for 48h; Heating;84%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

4-bromo-N-cyclohexylideneaniline
64456-62-8

4-bromo-N-cyclohexylideneaniline

C48H46N4

C48H46N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere;84%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

C33H21Br

C33H21Br

C90H60N2

C90H60N2

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene at 95 - 100℃; for 2.5h;84%
bromobenzene
108-86-1

bromobenzene

N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl
15546-43-7

N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In o-xylene; toluene at 110℃; for 24h; Inert atmosphere;82.62%
N,N'-diphenyl-p-phenylenediamine
531-91-9

N,N'-diphenyl-p-phenylenediamine

3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de]acridine
1224892-52-7

3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de]acridine

N4,N4'-Bis-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine
1319016-29-9

N4,N4'-Bis-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine

Conditions
ConditionsYield
Stage #1: N,N'-diphenyl-p-phenylenediamine; 3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de]acridine In 1,4-dioxane for 1h; Hartwig-buchwald coupling reaction; Inert atmosphere;
Stage #2: With sodium t-butanolate; tri-tert-butyl phosphine; palladium diacetate In 1,4-dioxane for 18h; Reflux;
81%

N,N'-Diphenylbenzidine Chemical Properties

The Molecular Structure of (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-diphenyl- (CAS NO.531-91-9):

Molecular Formula: C24H20N2
Molecular Weight: 336.429000 g/mol
IUPAC: 4-(4-anilinophenyl)-N-phenylaniline
Nominal Mass: 336 Da
Average Mass: 336.429 Da
Monoisotopic Mass: 336.162649 Da
Index of Refraction: 1.689
Molar Refractivity: 109.59 cm3
Molar Volume: 286.7 cm3
Surface Tension: 51.2 dyne/cm
Density: 1.173 g/cm3
Flash Point: 342 °C
Enthalpy of Vaporization: 81.13 kJ/mol
Boiling Point: 535 °C at 760 mmHg
Vapour Pressure: 1.6E-11 mmHg at 25°C 
InChI
InChI=1/C24H20N2/c1-3-7-21(8-4-1)25-23-15-11-19(12-16-23)20-13-17-24(18-14-20)26-22-9-5-2-6-10-22/h1-18,25-26H
Smiles
N(c1ccc(c2ccc(Nc3ccccc3)cc2)cc1)c1ccccc1

N,N'-Diphenylbenzidine Specification

 (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-diphenyl- (CAS NO.531-91-9) is also called as N,N'-Diphenylbenzidine ; AI3-18241 ; Diphenylbenzidine ; EINECS 208-521-7 ; NSC 4310 ; Benzidine, N,N'-diphenyl- (8CI) .

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