Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
N-trimethylsilylaniline
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid | |
With sulfuric acid | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With sulfuric acid at -20℃; |
N,N'-biphenyl-4,4'-diyl-di-anthranilic acid
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
at 285℃; | |
at 285℃; |
N,N'-dinitroso-N,N'-diphenyl-benzidine
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid Reduktion der entstandenen Loesung mit Zinkstaub; |
1,1-Diphenylhydrazine
A
N,N'-diphenyl-p-phenylenediamine
B
N-phenyl-1,2-benzenediamine
Conditions | Yield |
---|---|
With sulfuric acid at -16℃; |
Conditions | Yield |
---|---|
elektrolytische Oxydation und Reduktion des entstandenen kristallinischen Produkts mit Zink; |
Conditions | Yield |
---|---|
bei der Reduktion des entstandenen blauen Produkts mit NaHSO3 oder Zinkstaub; |
sulfuric acid
diphenylamine
A
N,N'-diphenyl-p-phenylenediamine
B
N,N'-dinitroso-N,N'-diphenyl-benzidine
C
N,N'-bis-(4-nitroso-phenyl)-benzidine
Conditions | Yield |
---|---|
bei folgendem Zusatz von Eis zum Reaktionsgemisch; |
sulfuric acid
sulfur trioxide
diphenylamine
A
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
at 80℃; | |
at 80℃; |
sulfuric acid
1,1-Diphenylhydrazine
A
N,N'-diphenyl-p-phenylenediamine
B
4-anilinophenol
C
N-phenyl-1,2-benzenediamine
Conditions | Yield |
---|---|
at -16℃; anschl. Erwaermen auf 20grad; |
sulfuric acid
tetraphenylhydrazine
acetic acid
benzene
A
N,N'-diphenyl-p-phenylenediamine
B
diphenylamine
Conditions | Yield |
---|---|
nachf. Reduktion mit Zinkstaub; |
tetraphenylhydrazine
benzene
A
N,N'-diphenyl-p-phenylenediamine
B
N-(4-chloro-phenyl)-N',N'-diphenyl-p-phenylenediamine
C
diphenylamine
Conditions | Yield |
---|---|
in Kohlendioxyd-Atmosphaere; |
sulfuric acid
N,N-diphenylhydroxylamine
A
N,N'-diphenyl-p-phenylenediamine
B
diphenylamine
Conditions | Yield |
---|---|
at -20℃; |
sulfuric acid
N,N'-dinitroso-N,N'-diphenyl-benzidine
acetic acid
N,N'-diphenyl-p-phenylenediamine
N-nitrosodiphenylamine
A
tetraphenylhydrazine
B
N,N'-diphenyl-p-phenylenediamine
C
diphenylamine
Conditions | Yield |
---|---|
With HY zeolite In dichloromethane at 20℃; Product distribution; Further Variations:; Reagents; Temperatures; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper; amyl alcohol 2: 285 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper; amyl alcohol 2: 285 °C View Scheme |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 3h; Electrolysis; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
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
N,N'-diphenyl-p-phenylenediamine
C62H48N2
Conditions | Yield |
---|---|
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In xylene at 125℃; for 15h; | 99% |
N,N'-diphenyl-p-phenylenediamine
1-bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene
Conditions | Yield |
---|---|
With di(tertbutyl)phenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux; | 99% |
N,N'-diphenyl-p-phenylenediamine
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
N,N'-diphenyl-N,N'-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-bromo-9,9'-spirobifluorene
Conditions | Yield |
---|---|
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
4-N,N-diphenylamino-1-bromobenzene
N',N"-bis[4-(diphenylamino)phenyl]-N',N"-diphenyl biphenyl-4,4'-diamine
Conditions | Yield |
---|---|
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
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 | Yield |
---|---|
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 72h; Ullmann reaction; Heating; | 90% |
N,N'-diphenyl-p-phenylenediamine
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 | Yield |
---|---|
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene Ullmann reaction; Heating; | 90% |
Conditions | Yield |
---|---|
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction; | 90% |
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
In perchloric acid; water; N,N-dimethyl-formamide Electrolysis; | 90% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; (1R,2R)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux; | 88% |
N,N'-diphenyl-p-phenylenediamine
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 | Yield |
---|---|
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene Ullmann reaction; Heating; | 87.5% |
Conditions | Yield |
---|---|
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
N,N'-diphenyl-p-phenylenediamine
N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine
Conditions | Yield |
---|---|
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 190℃; for 14h; Ullmann condensation; | 86% |
Conditions | Yield |
---|---|
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
N,N'-diphenyl-p-phenylenediamine
N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine
Conditions | Yield |
---|---|
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
N,N'-bis[(p-trifluorovinyloxy)phenyl]-N,N'-bis(phenyl)benzidine
Conditions | Yield |
---|---|
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
sodium p-chlorobenzenesulphinate
Conditions | Yield |
---|---|
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction; | 85% |
N,N'-diphenyl-p-phenylenediamine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In tetrahydrofuran for 48h; Heating; | 84% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene at 95 - 100℃; for 2.5h; | 84% |
bromobenzene
N,N'-diphenyl-p-phenylenediamine
N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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% |
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
(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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