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N,N'-Diphenylbenzidine
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Name

N,N'-Diphenylbenzidine

 EINECS 208-521-7
CAS No. 531-91-9 Density 1.173 g/cm3
PSA 24.06000 LogP 6.98680
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 N/A
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-;

Article Data 39

N,N'-Diphenylbenzidine Synthetic route

108-90-7

chlorobenzene

92-87-5

p,p'-diaminobiphenyl

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
92-86-4

4-(4-bromophenyl)bromobenzene

62-53-3

aniline

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%
92-86-4

4-(4-bromophenyl)bromobenzene

3768-55-6

N-trimethylsilylaniline

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%
108-86-1

bromobenzene

92-87-5

p,p'-diaminobiphenyl

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
122-39-4

diphenylamine

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;
632-52-0

tetraphenylhydrazine

531-91-9

N,N'-diphenyl-p-phenylenediamine

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

N,N-diphenylhydroxylamine

531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With sulfuric acid at -20℃;
53036-42-3

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

531-91-9

N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
at 285℃;
at 285℃;
40317-17-7

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

531-91-9

N,N'-diphenyl-p-phenylenediamine

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

tetrachloromethane

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

531-91-9

N,N'-diphenyl-p-phenylenediamine

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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