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603-34-9

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603-34-9 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 603-34-9 differently. You can refer to the following data:
1. Monoclinic crystals from EtOAc.
2. Triphenylamine is a colorless crystalline solid.

Uses

Different sources of media describe the Uses of 603-34-9 differently. You can refer to the following data:
1. Organic light-emitting diode (OLED) devices have received much attention, because they are expected to be a next generation display and light source, thanks to lightweight and flexible organic materials. Triphenylamine is a propeller-like structural chromophore with a nitrogen atom center. The compound has a large steric hindrance and hyper conjugation electronic effect, which can enhance the stability of the nitrogen atomic radical. Triphenylamine materials also have a high hole mobility due to their unique free radicals nature. Many hole transport materials based on triphenylamine derivatives (TPD) are widely usable,because they are heat-resistant and amorphous.In addition to the TPDs, oxadiazole derivatives (PBD) having an electron transport property, Alq3 as a host material,and blue emissive distylyl derivatives are fundamental materials for amorphous OLED devices. It is used in the manufacture of photographic film. Triphenylamines (TPAs) are highly fluorescent compounds that are efficient to induce cell death upon visible light excitation. Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate. It is coated on film bases as primary photoconductor.
2. It is coated on photographic film, where it acts as photoconductor.
3. Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate. It is coated on film bases as primary photoconductor.

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 86, 1983 DOI: 10.1139/v83-015Organic Syntheses, Coll. Vol. 1, p. 544, 1941

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Triphenylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

Triphenyl amine is considered to have low systemic toxicity, but it may act as a slight skin irritant. Adverse effects have not been reported in humans.

Fire Hazard

The flash point of Triphenylamine has not been determined, but Triphenylamine is probably combustible.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx. See also AROMATIC AMINES.

Potential Exposure

Triphenylamine is used as a primary photoconductor and in making photographic film coated on photographic film bases.

Carcinogenicity

Triphenyl amine was not mutagenic in bacterial assays with or without metabolic activation.

Purification Methods

Crystallise the amine from EtOH or from *benzene/absolute EtOH, diethyl ether and pet ether. It is sublimed under vacuum and carefully dried in a vacuum line. Store it in the dark under nitrogen. [Beilstein 12 IV 276.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxo acids, epoxides, aldehydes, ketones.

Check Digit Verification of cas no

The CAS Registry Mumber 603-34-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 3 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 603-34:
(5*6)+(4*0)+(3*3)+(2*3)+(1*4)=49
49 % 10 = 9
So 603-34-9 is a valid CAS Registry Number.
InChI:InChI=1/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H/p+1

603-34-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A15939)  Triphenylamine, 98%   

  • 603-34-9

  • 5g

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A15939)  Triphenylamine, 98%   

  • 603-34-9

  • 25g

  • 445.0CNY

  • Detail
  • Alfa Aesar

  • (A15939)  Triphenylamine, 98%   

  • 603-34-9

  • 100g

  • 1342.0CNY

  • Detail

603-34-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Triphenylamine

1.2 Other means of identification

Product number -
Other names Benzenamine, N,N-diphenyl-

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:603-34-9 SDS

603-34-9Synthetic route

bromobenzene
108-86-1

bromobenzene

diphenylamine
122-39-4

diphenylamine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 20℃; for 1h;99%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Time; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
aniline
62-53-3

aniline

chlorobenzene
108-90-7

chlorobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
With potassium tert-butylate In toluene at 135℃; for 36h;78%
With copper chromium oxide; potassium hydroxide In toluene for 18h; Ullmann Condensation; Inert atmosphere; Reflux; Green chemistry;43%
With bis-triphenylphosphine-palladium(II) chloride; (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol; sodium t-butanolate In o-xylene at 145℃; for 12h; Schlenk technique; Inert atmosphere;
diphenylamine
122-39-4

diphenylamine

chlorobenzene
108-90-7

chlorobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;99%
With C30H41ClPPd; sodium t-butanolate In toluene at 100℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;99%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 21h;98%
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

aniline
62-53-3

aniline

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 25℃; for 72h;98%
With cesium fluoride In acetonitrile at 20℃; for 72h;98%
iodobenzene
591-50-4

iodobenzene

aniline
62-53-3

aniline

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium tert-butylate; 1,2-bis(2,6-diisopropylphenylimino)ethane; copper(l) iodide In toluene at 120℃; for 48h;97%
With potassium tert-butylate In toluene at 120℃; for 12h; Ullmann coupling; Inert atmosphere;95%
With copper chromium oxide; potassium hydroxide In toluene for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Ullmann Condensation; Inert atmosphere; Reflux; Green chemistry;95%
bromobenzene
108-86-1

bromobenzene

N-(trimethylsilyl)-diphenylamine
17425-91-1

N-(trimethylsilyl)-diphenylamine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Inert atmosphere;97%
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Time; Inert atmosphere;97%
4-(diphenylamino)phenyl boronic acid
201802-67-7

4-(diphenylamino)phenyl boronic acid

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.166667h; Solvent; Reagent/catalyst;97%
With copper(ll) sulfate pentahydrate; oxygen; diisopropylamine In ethanol; water at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Green chemistry;96%
iodobenzene
591-50-4

iodobenzene

diphenylamine
122-39-4

diphenylamine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; ethylmagnesium bromide; triphenylphosphine In tetrahydrofuran at 80℃; for 3h;96%
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 0.666667h;96%
With potassium tert-butylate In toluene at 120℃; for 12h;95%
2-((4-diphenylamino)phenyl)[1,3,2]dioxaborolane
402488-98-6

2-((4-diphenylamino)phenyl)[1,3,2]dioxaborolane

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.233333h;96%
cyclohexanone
108-94-1

cyclohexanone

nitrobenzene
98-95-3

nitrobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With N/O-doped porous carbon (on base of polypyrrole) supported nanopalladium In toluene at 160℃; for 36h; Reagent/catalyst; Inert atmosphere; Sealed tube;96%
chlorobenzene
108-90-7

chlorobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium tert-butylate; urea; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 46h;95%
With ammonia; sodium; Petroleum ether
Multi-step reaction with 2 steps
1: sodium t-butanolate; (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl / neat (no solvent) / 12 h / 110 °C / Inert atmosphere; Green chemistry
2: sodium t-butanolate; (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl / neat (no solvent) / 12 h / 110 °C / Inert atmosphere; Green chemistry
View Scheme
iodobenzene
591-50-4

iodobenzene

aniline
62-53-3

aniline

A

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium tert-butylate; copper(l) iodide In toluene at 115℃; for 3.5h; Product distribution; Further Variations:; Reagents;A 95%
B 2%
With copper at 180℃; for 12h;A 46%
B 31%
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox;A 12%
B 39 %Chromat.
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 110℃; for 3.5h; Product distribution; Further Variations:; Catalysts; high pressure;
iodobenzene
591-50-4

iodobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium tetrachloropalladate(II); L-arginine; potassium hydroxide In water at 80℃; for 2h; Reagent/catalyst;95%
With potassium phosphate; copper(l) iodide; lithium amide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; chemoselective reaction;79%
Multi-step reaction with 2 steps
1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 24 h / Reflux
2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 144 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate / isopropyl alcohol / 6 h / 80 °C
2: Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate / isopropyl alcohol / 24 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: ammonia; potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry
2: potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry
3: potassium carbonate / water; ethanol / 20 °C / UV-irradiation; Green chemistry
View Scheme
phenyl copper
3220-49-3

phenyl copper

lithium diphenylamide
5856-89-3

lithium diphenylamide

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With chloranil at -60℃;94%
bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;92%
With dichloro{1,10-[dicyclohexylbenzyl]-3,3'-o-xylyldibenzimidazolidin-2,2'-diylidene}palladium (II); potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Buchwald-Hartwig amination; Inert atmosphere;92%
With potassium hydroxide In water for 24h; Buchwald-Hartwig reaction; Reflux; Inert atmosphere;88%
4-(diphenylamino)phenylboronic pinacol ester
267221-88-5

4-(diphenylamino)phenylboronic pinacol ester

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.916667h;92%
With copper(ll) sulfate pentahydrate; oxygen; diisopropylamine In ethanol; water at 80℃; for 24h; Green chemistry;61%
4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With 1,4-dioxane; 1,10-Phenanthroline; sodium hydride In mineral oil at 140℃; for 22h; Schlenk technique; Inert atmosphere;90%
With tributyl-amine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.8h; Inert atmosphere; Electrolysis;80%
With formic acid; C59H60N6O2Pt; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 4h; Inert atmosphere; Sealed tube; UV-irradiation;74 %Spectr.
diphenylamine
122-39-4

diphenylamine

1,4-Cyclohexanedione
637-88-7

1,4-Cyclohexanedione

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
toluene-4-sulfonic acid88.2%
toluene-4-sulfonic acid In toluene for 12h; Heating;88%
iodobenzene
591-50-4

iodobenzene

N-phenyl-1-naphthylamine
90-30-2

N-phenyl-1-naphthylamine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
potassium hydroxide; copper In various solvent(s) at 160℃; for 8h;88%
diphenylamine
122-39-4

diphenylamine

chlorobenzene
108-90-7

chlorobenzene

A

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

B

N-(2-biphenyl)aniline
35887-50-4

N-(2-biphenyl)aniline

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether; cyclohexane at 25℃; for 24h; Inert atmosphere;A n/a
B 87%
diphenylamine
122-39-4

diphenylamine

phenylboronic acid
98-80-6

phenylboronic acid

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With CoCuFe2O4; potassium hydroxide In ethanol at 60℃; for 5h; Green chemistry;85%
With potassium carbonate In ethanol; water at 70℃; for 8h; Chan-Lam Coupling;40 %Chromat.
bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

A

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With C46H58Br2N4O4Pd; potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Inert atmosphere; Buchwald-Hartwig amination;A 84%
B 16%
With water; sodium t-butanolate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;A 40%
B 60%
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; Product distribution; Further Variations:; Catalysts; high pressure;
bromobenzene
108-86-1

bromobenzene

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium tert-butylate; urea; tri tert-butylphosphoniumtetrafluoroborate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1,4-dioxane at 100℃; for 19h;83%
With potassium tert-butylate; urea; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 19h;83%
Multi-step reaction with 2 steps
1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 96 h / Reflux
2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 144 h / Reflux
View Scheme
nitrobenzene
98-95-3

nitrobenzene

diphenylamine
122-39-4

diphenylamine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;83%
With potassium phosphate; bis(acetylacetonato)palladium(II); BrettPhos In n-heptane at 130℃; for 24h;83%
tri(p-bromophenyl)amine
4316-58-9

tri(p-bromophenyl)amine

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 132h;82%
diphenylamine
122-39-4

diphenylamine

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

Conditions
ConditionsYield
With potassium hydroxide at 60℃; for 0.5h; Catalytic behavior; Green chemistry;81%
2-[10-(N-phenylamino)-1'-(4-nitrophenyl)]methylcyclohexanone

2-[10-(N-phenylamino)-1'-(4-nitrophenyl)]methylcyclohexanone

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

A

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

B

(E)-2-[(4-nitrophenyl)methylene]cyclohexanone
22114-45-0, 56005-41-5

(E)-2-[(4-nitrophenyl)methylene]cyclohexanone

C

6-(4-nitrophenyl)-5-phenyl-5,6,7,8,9,10-hexahydrophenanthridine

6-(4-nitrophenyl)-5-phenyl-5,6,7,8,9,10-hexahydrophenanthridine

Conditions
ConditionsYield
Stage #1: 2-[10-(N-phenylamino)-1'-(4-nitrophenyl)]methylcyclohexanone; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With potassium fluoride; 18-crown-6 ether In acetonitrile at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile for 1h; Inert atmosphere; Reflux;
A 15%
B 15%
C 80%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

tri(p-bromophenyl)amine
4316-58-9

tri(p-bromophenyl)amine

Conditions
ConditionsYield
With N-Bromosuccinimide; triethylamine In N,N-dimethyl-formamide at 20℃;100%
With bromine In chloroform at 0 - 20℃; for 1h;97%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12h; Cooling with ice;94%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

4-nitrophenyldiphenylamine
4316-57-8

4-nitrophenyldiphenylamine

Conditions
ConditionsYield
With sodium nitrate; acetic acid In chloroform at 85℃; Inert atmosphere;100%
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 3h; Ionic liquid;89%
With dinitrogen trioxide In dichloromethane at 0℃;42%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

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

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

Conditions
ConditionsYield
Stage #1: N,N-diphenylaminobenzene With methanesulfonic acid In dichloromethane at 0℃;
Stage #2: With chloranil In dichloromethane at 0 - 20℃; for 0.0166667h; Reagent/catalyst; Solvent; Time;
99%
With 5% rhodium-on-charcoal; trifluoroacetic acid at 50℃; for 1h; Reagent/catalyst; Green chemistry; regioselective reaction;99%
Stage #1: N,N-diphenylaminobenzene With copper(II) perchlorate In acetonitrile at 25℃; for 12h;
Stage #2: With potassium carbonate In water; acetonitrile at 25℃; for 0.5h; Further stages.;
81%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

tris(4-iodophenyl)amine
4181-20-8

tris(4-iodophenyl)amine

Conditions
ConditionsYield
Stage #1: N,N-diphenylaminobenzene With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 21h;
Stage #2: With water; sodium thiosulfate In dichloromethane
99%
Stage #1: N,N-diphenylaminobenzene With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 21h;
Stage #2: With sodium thiosulfate In dichloromethane; water
99%
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃;97%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

N,N-bis(4-bromophenyl)aniline
81090-53-1

N,N-bis(4-bromophenyl)aniline

Conditions
ConditionsYield
With N-Bromosuccinimide In ethyl acetate at 20℃; for 24h;99%
With N-Bromosuccinimide In ethyl acetate at 20℃; for 24h;99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 4h;90%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

(E)-tert-butyl (1-methyl-2-oxoindolin-3-ylidene)carbamate

(E)-tert-butyl (1-methyl-2-oxoindolin-3-ylidene)carbamate

tert-butyl (3-(4-(diphenylamino)phenyl)-1-methyl-2-oxoindolin-3-yl)carbamate

tert-butyl (3-(4-(diphenylamino)phenyl)-1-methyl-2-oxoindolin-3-yl)carbamate

Conditions
ConditionsYield
With C21H17F3OP(1+)*C32H12BF24(1-) In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Friedel-Crafts Alkylation;99%
1H-imidazole
288-32-4

1H-imidazole

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C39H21F18N7O6

C39H21F18N7O6

Conditions
ConditionsYield
Stage #1: 1H-imidazole; N,N-diphenylaminobenzene In acetonitrile for 0.5h;
Stage #2: trifluoroacetic anhydride In acetonitrile for 1.5h;
98.32%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

5-hexylbicyclo[2.2.1]hept-2-ene
22094-83-3

5-hexylbicyclo[2.2.1]hept-2-ene

polymer, Mw 1371000, Mn 349000; monomer(s): 5-hexyl-2-norbornene, 80 mol percent in feed; N,N-diphenylaniline, 20 mol percent in feed

polymer, Mw 1371000, Mn 349000; monomer(s): 5-hexyl-2-norbornene, 80 mol percent in feed; N,N-diphenylaniline, 20 mol percent in feed

Conditions
ConditionsYield
{(η6-toluene)Ni(C6F5)2} In toluene at 20℃; for 24h;98%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

tris(phenyl-2,4,6-d3)amine
21223-02-9

tris(phenyl-2,4,6-d3)amine

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; water-d2 In chloroform-d1 at 80℃; for 24h; Sealed tube; regioselective reaction;98%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: N,N-diphenylaminobenzene In 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere;
97.6%
With trichlorophosphate at 35 - 40℃; Inert atmosphere;96%
Stage #1: N,N-diphenylaminobenzene; N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0 - 45℃; Vilsmeier-Haack reaction;
Stage #2: With water In 1,2-dichloro-ethane Vilsmeier-Haack reaction; Cooling with ice;
96%
tricyanomethane
454-50-2

tricyanomethane

N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

triphenylammonium tricyanomethanide

triphenylammonium tricyanomethanide

Conditions
ConditionsYield
In water at 50℃; for 3h;97%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

chloranil
118-75-2

chloranil

A

2,3,5,6-tetrachlorobenzene-1,4-diol
87-87-6

2,3,5,6-tetrachlorobenzene-1,4-diol

B

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

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

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.0166667h; Molecular sieve;A 96%
B 83%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

4-(diphenylamino)benzaldehyde
4181-05-9

4-(diphenylamino)benzaldehyde

Conditions
ConditionsYield
With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Reflux;95%
Stage #1: N,N-diphenylaminobenzene With trichlorophosphate In N,N-dimethyl-formamide for 1h;
Stage #2: With sodium hydroxide
85%
With N,N-dimethyl-formamide; trichlorophosphate at 100℃; for 6h;52.74%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

acetyl chloride
75-36-5

acetyl chloride

(1,1',1''-[nitrilotri(4,1-phenylene)]tri(ethan-1-one))
4181-21-9

(1,1',1''-[nitrilotri(4,1-phenylene)]tri(ethan-1-one))

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation; Inert atmosphere;95%
With aluminum (III) chloride In dichloromethane at 0℃; for 12h;95%
With aluminum (III) chloride In dichloromethane Reflux;92%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

2,7-dibromo-(9-phenyl-9H-fluoren-9-ol)
132717-37-4

2,7-dibromo-(9-phenyl-9H-fluoren-9-ol)

tris(4-(2,7-dibromo-9-phenyl-9H-fluoren-9-yl)phenyl)amine

tris(4-(2,7-dibromo-9-phenyl-9H-fluoren-9-yl)phenyl)amine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;95%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

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

4-N,N-diphenylamino-1-bromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane for 4h; Reflux;94%
With N-Bromosuccinimide In tetrachloromethane for 4h; Heating;93%
With N-Bromosuccinimide In tetrachloromethane for 4h; Inert atmosphere; Reflux;93%

603-34-9Relevant articles and documents

An Investigation into the Electrochemical Oxidation of Some Aromatic Amines in the Room-Temperature Molten Salt System Aluminium Chloride-n-Butylpyridinium Chloride

Robinson, J.,Osteryoung, R. A.

, p. 4415 - 4420 (1980)

The electrochemical oxidation of a number of aromatic amines in the low-temperature molten salt system aluminium chloride-N-butylpyridinium chloride has been investigated.In acidic melts TPA is oxidized reversibly to its radical cation which at more positive potentials undergoes a further, chemically irreversibly oxidation to the dication of the amine.In basic melts the stability of the radical cation is reduced and it couples to form tetraphenylbenzidine which is itself further oxidized.The oxidation of the other amines was more complex as a result of their being involved in complexation equilibria with acid species in the melt.In basic melts where they were uncomplexed, their behavior was similar to that of TPA, but, in acidic melts, the amine complexes underwent irreversible two-electron oxidations to their respective dications at potentials ca. 1 V positive of the first oxidation potential of the free amine.TMB, which, depending on the melt acidity, could be present as the free amine mono or di complex, was also oxidized to its dication.The actual mechanism of this oxidation was dependent upon the melt acidity.The oxidation of TMB was also shown to be dependent upon the temperature, the TMB cation radical being stable at low temperature but becoming unstable with respect to disproportionation as the temperature was increased.

Nakano et al.

, p. 1,5 (1979)

Laser flash photolysis generation and kinetic studies of corrole-manganese(v)-oxo intermediates

Zhang, Rui,Harischandra, Dilusha N.,Newcomb, Martin

, p. 5713 - 5720 (2005)

Corrole-manganese(V)-oxo intermediates were produced by laser flash photolysis of the corresponding corrole-manganese(IV) chlorate complexes, and the kinetics of their decay reactions in CH2Cl2 and their reactions with organic reductants were studied. The corroie ligands studied were 5,10,15-tris(pentafluorophenyl)corrole (H3TPFC), 5,10,15-triphenylcorrole (H3TPC), and 5,15-bis(pentafluorophenyl)-10- (p-methoxyphenyl)corrole (H3BPFMC). In self-decay reactions and in reactions with substrates, the order of reactivity of (Cor)MnV(O) was TPC > BPFMC > TPFC, which is inverted from that expected based on the electron-demand of the ligands. The rates of reactions of (Cor)MnV(O) were dependent on the concentration of the oxidant and other manganese species, with increasing concentrations of various manganese species resulting in decreasing rates of reactions, and the apparent rate constant for reaction of (TPFC)MnV(O) with triphenylamine was found to display fractional order with respect to the manganese-oxo species. The kinetic results are consistent in part with a reaction model involving disproportionation of (Cor)MnV(O) to give (Cor)MnIV and (Cor)MnVI(O) species, the latter of which is the active oxidant. Alternatively, the results are consistent with oxidation by (Cor)MnV(O) which is reversibly sequestered in non-reactive complexes by various manganese species.

Method for synthesizing organic aromatic nitrogen-containing compound by taking nitrogen as nitrogen source

-

Paragraph 0034-0039, (2021/05/08)

The invention provides a method for synthesizing an organic aromatic nitrogen-containing compound by taking nitrogen as a nitrogen source, and belongs to the field of organic synthesis. The invention provides a method for synthesizing an organic aromatic nitrogen-containing compound by taking nitrogen as a nitrogen source, which is characterized by comprising the following steps of: 1, reducing nitrogen by lithium powder to form lithium nitride; and 2, reacting the lithium nitride with a halogenated aromatic compound under the action of a transition metal catalyst, a ligand, alkali and a phase transfer catalyst to obtain an organic aromatic nitrogen-containing compound; wherein the two steps of reactions are completed in one pot. The method realizes the conversion of cheap nitrogen to the high-added-value aromatic nitrogen-containing compound, and also has the advantages of mild reaction conditions, good compatibility of substrate functional groups, high yield and the like.

Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules

Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip

, (2020/11/05)

Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.

A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework

Ma, Ruixuan,Qin, Jianhua,Shi, Lei,Zhang, Xinhai

, p. 795 - 799 (2021/07/06)

A new copper(II) metal-organic framework is constructed as a sustainable copper heterogeneous catalyst. Cu-DPTCA, with high catalytic activity, can effectively promote the Chan–Lam coupling reaction of arylboronic acids and amines without adding any base or additive.

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