531-91-9

Basic information

• Product Name: N,N'-Diphenylbenzidine
• Synonyms: N,N'-DIPHENYLBENZIDINE;N,N'-DIPHENYL BIPHENYLAMINE;SYM-DIPHENYLBENZIDINE;TIMTEC-BB SBB002946;(4),N(4')-Diphenyl-biphenyl-4,4'-diamine;1’-biphenyl]-4,4’-diamine,n,n’-diphenyl-[;Benzidine, N,N'-diphenyl-;Diphenylbenzidine
• CAS NO: 531-91-9
• Molecular Formula: C₂₄H₂₀N₂
• Molecular Weight: 336.43
• EINECS: 208-521-7
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;C11 to C38Titration;Amines;Indicators;Nitrogen Compounds;Redox Indicators;C20 to C30+;Analytical Reagents;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Redox Indicators;Titration
• Mol File: 531-91-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 246-248 °C(lit.)
• Boiling Point: 462.9°C (rough estimate)
• Flash Point: >110°C
• Appearance: Gray to brownish/Fine Crystalline Powder
• Density: 1.1750 (rough estimate)
• Vapor Density: 11.6 (vs air)
• Refractive Index: 1.7620 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Acetone (Slightly), DMF (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, So
• PKA: 1.31±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• Merck: 14,3319
• BRN: 2220993
• CAS DataBase Reference: N,N'-Diphenylbenzidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diphenylbenzidine(531-91-9)
• EPA Substance Registry System: N,N'-Diphenylbenzidine(531-91-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• RIDADR: 2811
• WGK Germany: 3
• F: 8
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 531-91-9(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Analysis:
N,N'-Diphenylbenzidine is used as an indicator for redox titrations, particularly with dichromate or cerium(IV) sulfate. Its ability to change color during the titration process helps in determining the endpoint of the reaction accurately.
2. Used in Organic Synthesis:
N,N'-Diphenylbenzidine serves as an intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to be a valuable building block in the creation of a wide range of molecules.
3. Used in Dye Manufacturing:
N,N'-Diphenylbenzidine is also utilized in the production of dyes, specifically as a precursor for the synthesis of diphenylamine dyes. These dyes find applications in various industries, including textiles, plastics, and printing.
4. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N,N'-Diphenylbenzidine has been historically used in the pharmaceutical industry as a starting material for the synthesis of certain drugs. However, it is important to note that its use in this context has been limited due to concerns about its potential carcinogenic properties.

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.]

Synthetic route

chlorobenzene (108-90-7) + p,p'-diaminobiphenyl (92-87-5) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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

4-(4-bromophenyl)bromobenzene (92-86-4) + aniline (62-53-3) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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 (92-86-4) + N-trimethylsilylaniline (3768-55-6) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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%

bromobenzene (108-86-1) + p,p'-diaminobiphenyl (92-87-5) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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

diphenylamine (122-39-4) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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;

tetraphenylhydrazine (632-52-0) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
With sulfuric acid; acetic acid
With sulfuric acid
With hydrogenchloride

N,N-diphenylhydroxylamine (1079-64-7) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
With sulfuric acid at -20℃;

N,N'-biphenyl-4,4'-diyl-di-anthranilic acid (53036-42-3) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
at 285℃;
at 285℃;

N,N'-dinitroso-N,N'-diphenyl-benzidine (40317-17-7) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
With sulfuric acid; acetic acid Reduktion der entstandenen Loesung mit Zinkstaub;

tetrachloromethane (56-23-5) + 1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane → N,N'-diphenyl-p-phenylenediamine (531-91-9)

1,1-Diphenylhydrazine (530-50-7) → N,N'-diphenyl-p-phenylenediamine (531-91-9) + N-phenyl-1,2-benzenediamine (534-85-0)

Conditions	Yield
With sulfuric acid at -16℃;

acetic acid (64-19-7) + 1,2,15,16-tetraphenyl-1,2,15,16-tetraaza-[2.0.2.0]paracyclophane + zinc → N,N'-diphenyl-p-phenylenediamine (531-91-9)

sulfuric acid (7664-93-9) + diphenylamine (122-39-4) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
elektrolytische Oxydation und Reduktion des entstandenen kristallinischen Produkts mit Zink;

sulfuric acid (7664-93-9) + diphenylamine (122-39-4) + sodium dichromate → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
bei der Reduktion des entstandenen blauen Produkts mit NaHSO3 oder Zinkstaub;

sulfuric acid (7664-93-9) + diphenylamine (122-39-4) + sodium nitrite → N,N'-diphenyl-p-phenylenediamine (531-91-9) + N,N'-dinitroso-N,N'-diphenyl-benzidine (40317-17-7) + N,N'-bis-(4-nitroso-phenyl)-benzidine (88855-71-4)

Conditions	Yield
bei folgendem Zusatz von Eis zum Reaktionsgemisch;

sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + diphenylamine (122-39-4) → N,N'-diphenyl-p-phenylenediamine (531-91-9) + N.N'-diphenyl-benzidine sulfone

Conditions	Yield
at 80℃;
at 80℃;

sulfuric acid (7664-93-9) + 1,1-Diphenylhydrazine (530-50-7) → N,N'-diphenyl-p-phenylenediamine (531-91-9) + 4-anilinophenol (122-37-2) + N-phenyl-1,2-benzenediamine (534-85-0)

Conditions	Yield
at -16℃; anschl. Erwaermen auf 20grad;

sulfuric acid (7664-93-9) + tetraphenylhydrazine (632-52-0) + acetic acid (64-19-7) + benzene (71-43-2) → N,N'-diphenyl-p-phenylenediamine (531-91-9) + diphenylamine (122-39-4)

Conditions	Yield
nachf. Reduktion mit Zinkstaub;

tetraphenylhydrazine (632-52-0) + benzene (71-43-2) + etheric hydrochloric acid → N,N'-diphenyl-p-phenylenediamine (531-91-9) + N-(4-chloro-phenyl)-N',N'-diphenyl-p-phenylenediamine (857468-42-9) + diphenylamine (122-39-4)

Conditions	Yield
in Kohlendioxyd-Atmosphaere;

sulfuric acid (7664-93-9) + N,N-diphenylhydroxylamine (1079-64-7) → N,N'-diphenyl-p-phenylenediamine (531-91-9) + diphenylamine (122-39-4)

Conditions	Yield
at -20℃;

sulfuric acid (7664-93-9) + N,N'-dinitroso-N,N'-diphenyl-benzidine (40317-17-7) + acetic acid (64-19-7) + zinc → N,N'-diphenyl-p-phenylenediamine (531-91-9)

N-nitrosodiphenylamine (382165-80-2) → tetraphenylhydrazine (632-52-0) + N,N'-diphenyl-p-phenylenediamine (531-91-9) + diphenylamine (122-39-4)

Conditions	Yield
With HY zeolite In dichloromethane at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;

p,p'-diaminobiphenyl (92-87-5) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; copper; amyl alcohol 2: 285 °C View Scheme

ortho-chlorobenzoic acid (118-91-2) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; copper; amyl alcohol 2: 285 °C View Scheme

diphenylamine (122-39-4) → p,p'-(N,N'-diphenyl)diaminobis(phenyl)amine + tetraphenylhydrazine (632-52-0) + N,N'-diphenyl-p-phenylenediamine (531-91-9)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Electrolysis;

aniline (62-53-3) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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

4-chloro-aniline (106-47-8) → N,N'-diphenyl-p-phenylenediamine (531-91-9)

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

N,N'-diphenyl-p-phenylenediamine (531-91-9) + 1-bromo-3-(2-(2-methoxyethoxy)ethoxy)benzene → C46H48N2O6

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 (318261-63-1) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → C50H56N2O8

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 (954137-80-5) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → C62H48N2 (954137-37-2)

Conditions	Yield
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) + 1-bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene (125808-05-1) → C50H56N2O8

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 (531-91-9) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → N,N'-diphenyl-N,N'-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine (1416621-06-1)

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%

1-Bromonaphthalene (90-11-9) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl

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 (531-91-9) + 2-bromo-9,9'-spirobifluorene (171408-76-7) → 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]-1,1'-biphenyl

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 (531-91-9) + 4-N,N-diphenylamino-1-bromobenzene (36809-26-4) → N',N"-bis[4-(diphenylamino)phenyl]-N',N"-diphenyl biphenyl-4,4'-diamine (209980-53-0)

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 (531-91-9) + 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	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 (531-91-9) + 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	Yield
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) + sodium benzenesulfonate (873-55-2) → N,N′-diphenyl-3-(phenylsulfonyl)-[1,1′-biphenyl]-4,4′-diamine

Conditions	Yield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;	90%

N,N'-diphenyl-p-phenylenediamine (531-91-9) + sodium 4-methylbenzenesulfinate (824-79-3) → N,N′-diphenyl-3-tosyl-[1,1′-biphenyl]-4,4′-diamine

Conditions	Yield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;	90%

N,N'-diphenyl-p-phenylenediamine (531-91-9) → C48H36N4

Conditions	Yield
In perchloric acid; water; N,N-dimethyl-formamide Electrolysis;	90%

N,N'-diphenyl-p-phenylenediamine (531-91-9) + C11H7BrN2O2 → C46H32N6O4

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 (531-91-9) + 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	Yield
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) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → C52H42N4

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 (624-31-7) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (20441-06-9)

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

C12H14BrN + N,N'-diphenyl-p-phenylenediamine (531-91-9) → C48H46N4

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 (4214-28-2) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine (122738-25-4)

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 (531-91-9) + 1-bromo-4-(trifluorovinyloxy)benzene → N,N'-bis[(p-trifluorovinyloxy)phenyl]-N,N'-bis(phenyl)benzidine (1159606-87-7)

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 (531-91-9) + sodium p-chlorobenzenesulphinate (14752-66-0) → 3-[(4-chlorophenyl)sulfonyl]-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine

Conditions	Yield
In aq. phosphate buffer; acetonitrile Electrolysis; regioselective reaction;	85%

N,N'-diphenyl-p-phenylenediamine (531-91-9) → polymer; monomer(s): N-methyl-3,4-bis-(4-bromophenyl)maleimide; N,N\-diphenylbenzidine

Conditions	Yield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In tetrahydrofuran for 48h; Heating;	84%

N,N'-diphenyl-p-phenylenediamine (531-91-9) + 4-bromo-N-cyclohexylideneaniline (64456-62-8) → C48H46N4

Conditions	Yield
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) + C33H21Br → C90H60N2

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

bromobenzene (108-86-1) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl (15546-43-7)

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 (531-91-9) + 3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de]acridine (1224892-52-7) → N4,N4'-Bis-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine (1319016-29-9)

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%

Upstream product

• 632-52-0 tetraphenylhydrazine 
• 530-50-7 1,1-Diphenylhydrazine 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 122-39-4 diphenylamine 
• 7446-11-9 sulfur trioxide 
• 71-43-2 benzene 
• 1079-64-7 N,N-diphenylhydroxylamine 
• 40317-17-7 N,N'-dinitroso-N,N'-diphenyl-benzidine 
• 382165-80-2 N-nitrosodiphenylamine 
• 108-86-1 bromobenzene 
• 92-87-5 p,p'-diaminobiphenyl 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 

Downstream Products

• 134008-76-7 N,N’-bis(biphenyl-4-yl)-N,N’-diphenylbenzidine 
• 99328-86-6 diquinonediimine 
• 40317-17-7 N,N'-dinitroso-N,N'-diphenyl-benzidine 
• 115080-50-7 [3,3']bicyclohexa-1,4-dienylidene-6,6'-dione-bis-(N-phenyl oxime ) 
• 88855-71-4 N,N'-bis-(4-nitroso-phenyl)-benzidine 
• 27164-41-6 N,N′-dimethyl-N,N′-diphenylbenzidine 
• 184104-81-2 N⁴,N^4'-Diphenyl-N⁴-m-tolyl-biphenyl-4,4'-diamine 
• 477855-68-8 N,N'-diphenyl-N,N'-bis(2-phenacetyl)benzidine 
• 113664-24-7 N,N,N′,N′-tetrakis(4-bromophenyl)[1,1′-biphenyl]-4,4′-diamine 
• 640756-41-8 N,N,N',N'-tetrakis-(p-allylphenyl)-biphenyl-4,4'-diamine 
• 896427-55-7 N,N'-(diphenyl)(4-hydroxybiphenyl)benzidine 
• 851767-73-2 C₅₆H₃₆N₂ 
• 139255-23-5 4,4'-Bis[N-(8-fluoranthenyl)-N-phenylamino]biphenyl 
• 949462-13-9 C₅₆H₄₀N₂ 

Relevant articles and documents

The protonation and benzidine rearrangement of tetraphenylhydrazine

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.

Organic electroluminescent compound based on symmetric aromatic amine structure

The invention discloses an organic electroluminescent compound based on a symmetric aromatic amine structure. The structural formula of the organic electroluminescent compound is shown as a general formula (I) which is described in the specification. The organic electroluminescent compound has the advantages of high glass transition temperature, good thermal stability and high refractive index. When the compound is applied to an organic electroluminescent device, under the same current density, the luminous efficiency is improved to a certain extent, the starting voltage of the device is reduced, the power consumption is relatively reduced, and the service life is correspondingly prolonged.

Arylamine compound of imidazopyridine, and application thereof

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.

ORGANIC LIGHT-EMITTING DEVICE AND LIGHT-EMITTING APPARATUS INCLUDING THE SAME

Provided are an organic light-emitting device including a capping layer including an amine-based compound represented by a set or predetermined formula and a radical scavenger, and a light-emitting apparatus including the organic light-emitting device. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer a capping layer on the second electrode, wherein the capping layer includes the amine-based compound.

Aromatic amine derivative and organic light-emitting device using same

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.

ORGANIC COMPOUND AND LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DIODE DISPLAY DEVICE USING THE SAME

The present invention relates to an organic compound in which at least one diphenylmethylene fluorenyl group is directly or indirectly connected to a nitrogen atom constituting at least one amine group. The organic compound according to the present invention has excellent hole injection properties and/or hole transporting properties, and has excellent thermal stability. Accordingly, the organic compound of the present invention, when used in a hole layer, an electron blocking layer and/or a charge generation layer of a light-emitting device, can drive the light-emitting device by securing a sufficient current density at a low voltage. Even when the temperature increases according to driving of the light-emitting device, the compound of the present invention does not become deformed nor degraded, and can reduce stress transferred to the light-emitting device due to low-voltage driving. Accordingly, the organic compound of the present invention can be applied to embody a light-emitting diode and a display device having good luminous efficiency.(110) First electrode(120) Second electrodeCOPYRIGHT KIPO 2018

One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination

A methodology for a sequential palladium-catalyzed cross-coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi-aryl backbones. The linchpin of this development is the meta-terarylphosphine ligand, Cy*Phine, which has been employed as an air- and moisture-stable precatalyst, Pd(Cy*Phine)2Cl2, to improve the efficiency of one-pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd-Cy*Phine system could be tuned to furnish a one-pot, borylation–Suzuki reaction–amination (BSA) cross-coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three-step sequence in a single pot. (Figure presented.).

Metal-Free Oxidative C-C Coupling of Arylamines Using a Quinone-Based Organic Oxidant

A variety of arylamines are shown to undergo oxidative C-C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal-free) oxidant system to afford benzidines/naphthidines. Arylamines (3°/2°) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C-C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.

Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

Thianthrene has been synthesized by reacting diphenyl sulfide with AlCl3 in heptane at 98°C for 8 h at a diphenyl sulfide: AlCl3 molar ratio of 2: 1; the thianthrene yield is 58%. The reaction mechanism proposed previously has been confirmed by quantum-chemical calculations; the reaction is characterized by a low negative value of Gibbs free energy, a low heat of reaction, and a high activation energy of the first step. Diphenyl ether and diphenylamine do not enter the test reaction because of low nucleophilicity of the heteroatoms; diphenylamine dimerizes under the reaction conditions to form N,N′-diphenylbenzidine.

Iron-catalyzed aromatic amination for nonsymmetrical triarylamine synthesis

Novel iron-catalyzed amination reactions of various aryl bromides have been developed for the synthesis of diaryl- and triarylamines. The key to the success of this protocol is the use of in situ generated magnesium amides in the presence of a lithium halide, which dramatically increases the product yield. The present method is simple and free of precious and expensive metals and ligands, thus providing a facile route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.