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531-91-9 Usage

Chemical Properties

GREY TO BROWNISH FINE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 531-91-9 differently. You can refer to the following data:
1. See diphenylamine.
2. N,N'-Diphenylbenzidine is an indicator suitable for redox titrations, e.g. with dichromate or cerium(IV) sulfate 1,2. It is also used as intermediates in organic synthesis.

Synthesis

The synthesis of N,N'-Diphenylbenzidine is as follows:3.12 g (10mmol) of 4,4'-dibromodiphenyl, 2.3 mL (25 mmol) of aniline, 2.9 g (30 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, and 20 mg (0.1 mmol) of P(t-Bu)3?were dissolved in 30 mL of toluene, and then stirred at 90°C for 3 hrs. The reaction mixture was cooled to room temperature and three times extracted with distilled water and diethyl ether. Precipitates in an organic layer were filtered, washed with acetone and diethyl ether, and then dried in vacuum to obtain 0.3g of the intermediate compound C (yield: 90%).

Purification Methods

Crystallise the benzidine from toluene or ethyl acetate. Store it in the dark. [Beilstein 13 H 223, 13 IV 368.]

Check Digit Verification of cas no

The CAS Registry Mumber 531-91-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 1 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 531-91:
(5*5)+(4*3)+(3*1)+(2*9)+(1*1)=59
59 % 10 = 9
So 531-91-9 is a valid CAS Registry Number.

531-91-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A13802)  N,N'-Diphenylbenzidine, 98%   

  • 531-91-9

  • 5g

  • 437.0CNY

  • Detail
  • Alfa Aesar

  • (A13802)  N,N'-Diphenylbenzidine, 98%   

  • 531-91-9

  • 25g

  • 1910.0CNY

  • Detail
  • Aldrich

  • (D205206)  N,N′-Diphenylbenzidine  97%

  • 531-91-9

  • D205206-10G

  • 780.39CNY

  • Detail

531-91-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N'-Diphenylbenzidine

1.2 Other means of identification

Product number -
Other names 4-(4-anilinophenyl)-N-phenylaniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:531-91-9 SDS

531-91-9Synthetic 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
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%

531-91-9Relevant articles and documents

The protonation and benzidine rearrangement of tetraphenylhydrazine

Svanholm, Ulla,Parker, Vernon D.

, p. 440 - 441 (1972)

Tetraphenylhydrazine is stable at 0 °C in trifluoroacetic acid-antimony pentafluoride and can be recovered by caustic quench at low temperature but rapidly rearranges to NN'-diphenylbenzidine at room temperature.

Arylamine compound of imidazopyridine, and application thereof

-

Paragraph 0053-0056, (2021/06/12)

The invention relates to an arylamine compound ofimidazopyridine, and application thereof. The compound has a structure as shown in a formula (I). The compound disclosed by the invention has the advantages of low sublimation temperature, good thermal stability, high refractive index, small refractive index difference in a visible region and the like, can be used as a light extraction layer material and is applied to an organic light-emitting device.

Aromatic amine derivative and organic light-emitting device using same

-

Paragraph 0061-0063, (2018/03/01)

The invention provides an aromatic amine derivative and an organic light-emitting device using the same and relates to the technical field of organic optoelectronic materials. Carbazole structures have higher redox potential values and good stability under air or illumination conditions. Therefore, by introducing the carbazole structures, the obtained aromatic amine derivative disclosed by the invention shows good thermal stability, can be used for preparing the organic light-emitting device and particularly shows the advantages of high efficiency and low driving voltage when being used as a hole transmission material in the organic light-emitting device; the aromatic amine derivative is an organic light-emitting material with excellent performance; the organic light-emitting device disclosed by the invention is superior to an existing common OLED (Organic Light Emitting Diode) device.

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