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N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine, commonly known as TPD, is a synthetic organic compound that serves as a crucial component in the development of organic electronic devices. It is characterized by its ability to efficiently transport holes, making it an indispensable material for various applications within the electronics industry.

65181-78-4

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65181-78-4 Usage

Uses

Used in Organic Electronics Industry:
N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine is used as a hole transport material for its exceptional charge transport properties, which are vital for the performance of organic electronic devices.
Used in Electrophotographic Photoconductors:
In the field of xerography, TPD is utilized as a hole transport material for electrophotographic photoconductors. Its role in this application is to facilitate the transfer of charges, which is essential for the creation of high-quality images.
Used as an Organic Photoconductor:
TPD is employed as an organic photoconductor, where its ability to transport holes upon exposure to light is leveraged to improve the efficiency and performance of devices such as photocopiers and laser printers.
Used as a Hole Transporter:
N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine functions as a hole transporter in various electronic applications, ensuring the efficient movement of positive charge carriers and contributing to the overall effectiveness of the devices in which it is used.

Check Digit Verification of cas no

The CAS Registry Mumber 65181-78-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,1,8 and 1 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 65181-78:
(7*6)+(6*5)+(5*1)+(4*8)+(3*1)+(2*7)+(1*8)=134
134 % 10 = 4
So 65181-78-4 is a valid CAS Registry Number.

65181-78-4SDS

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 N,N'-Bis(3-methylphenyl)-N,N'-diphenylbenzidine

1.2 Other means of identification

Product number -
Other names N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine

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:65181-78-4 SDS

65181-78-4Synthetic route

meta-bromotoluene
591-17-3

meta-bromotoluene

chlorobenzene
108-90-7

chlorobenzene

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; ruphos In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;98%
C40H32N2O4

C40H32N2O4

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With copper(I) oxide; N,N,N,N,-tetramethylethylenediamine at 200℃; for 4h; Temperature; Large scale;93.5%
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

3-Methyldiphenylamine
1205-64-7

3-Methyldiphenylamine

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 120℃; for 3h;91%
Stage #1: 3-Methyldiphenylamine With n-butyllithium
Stage #2: 4-(4-bromophenyl)bromobenzene With bis[tris(2-methylphenyl)phosphine]palladium In toluene at 100℃;
87%
With sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 20 - 130℃; Inert atmosphere;85.2%
4,4'-diiodobiphenyl
3001-15-8

4,4'-diiodobiphenyl

3-Methyldiphenylamine
1205-64-7

3-Methyldiphenylamine

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With potassium hydroxide; 1,10-Phenanthroline; copper(l) chloride In toluene at 125℃; for 5h; Ullmann condensation;85%
With copper; potassium carbonate; PEG-6000 In 1,2-dichloro-benzene for 22h; Heating / reflux;
CT-73; mixture of

CT-73; mixture of

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
In n-heptane Purification / work up;84.4%
4,4'-diiodobiphenyl
3001-15-8

4,4'-diiodobiphenyl

3-Methyldiphenylamine
1205-64-7

3-Methyldiphenylamine

4-methyldiphenylamine
620-84-8

4-methyldiphenylamine

A

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

B

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

C

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine

Conditions
ConditionsYield
With copper; potassium carbonate; polyethylene glycol at 90 - 205℃; for 17h; Heating / reflux;
Stage #1: 4,4'-diiodobiphenyl; 3-Methyldiphenylamine; 4-methyldiphenylamine With copper; PEG-6000 at 100℃; Neat (no solvent);
Stage #2: With potassium carbonate at 205℃; for 14h; Neat (no solvent);
4,4'-diiodobiphenyl
3001-15-8

4,4'-diiodobiphenyl

N-methyl-N-phenyl-3-toluidine
92115-21-4

N-methyl-N-phenyl-3-toluidine

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With copper; potassium carbonate; polyethylene glycol In 1,2-dichloro-benzene for 22h; Heating / reflux;
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

3-Methyldiphenylamine
1205-64-7

3-Methyldiphenylamine

diphenylamine
122-39-4

diphenylamine

A

N,N,N'-tris-(phenyl)-N'-(m-tolyl)-benzidine

N,N,N'-tris-(phenyl)-N'-(m-tolyl)-benzidine

B

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

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

C

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With potassium hydroxide; copper In Soltrol/70 at 165℃; for 7h; Product distribution / selectivity;
tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl at 139℃; for 6.5h; Product distribution / selectivity;
With calcium carbonate; zinc; 1,10-Phenanthroline; copper diacetate In xylene at 120℃; for 10.5h; Product distribution / selectivity;
ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; copper; copper(II) oxide / water / 105 °C / Large scale
2: caesium carbonate; copper; copper(II) oxide / nitrobenzene / 3 h / 200 °C / Large scale
3: copper(I) oxide; N,N,N,N,-tetramethylethylenediamine / 4 h / 200 °C / Large scale
View Scheme
2-(m-tolylamino)benzoic acid
16524-22-4

2-(m-tolylamino)benzoic acid

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; copper; copper(II) oxide / nitrobenzene / 3 h / 200 °C / Large scale
2: copper(I) oxide; N,N,N,N,-tetramethylethylenediamine / 4 h / 200 °C / Large scale
View Scheme
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; copper; copper(II) oxide / water / 105 °C / Large scale
2: caesium carbonate; copper; copper(II) oxide / nitrobenzene / 3 h / 200 °C / Large scale
3: copper(I) oxide; N,N,N,N,-tetramethylethylenediamine / 4 h / 200 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: palladium on activated charcoal; toluene-4-sulfonic acid / 1,3,5-trimethyl-benzene / 18 h / 160 °C / 760.05 Torr / Inert atmosphere; Schlenk technique
2: palladium on activated charcoal; toluene-4-sulfonic acid / 1,3,5-trimethyl-benzene / 18 h / 160 °C / 760.05 Torr / Inert atmosphere; Schlenk technique
View Scheme
cyclohexanone
108-94-1

cyclohexanone

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium on activated charcoal; toluene-4-sulfonic acid / 1,3,5-trimethyl-benzene / 18 h / 160 °C / 760.05 Torr / Inert atmosphere; Schlenk technique
2: palladium on activated charcoal; toluene-4-sulfonic acid / 1,3,5-trimethyl-benzene / 18 h / 160 °C / 760.05 Torr / Inert atmosphere; Schlenk technique
View Scheme
1H-imidazole
288-32-4

1H-imidazole

4,4'-bis(m-tolylphenylamino)biphenyl
65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C66H40F24N10O8
1204829-13-9

C66H40F24N10O8

Conditions
ConditionsYield
In acetonitrile Inert atmosphere;99.1%
In acetonitrile for 1.5h; Reflux; Inert atmosphere;

65181-78-4Relevant articles and documents

Electron Spin Resonance Spectroscopic Study of Electronic Charge Transport in an Aromatic Diamine

Veregin, Richard P.,Harbour, John R.

, p. 6231 - 6237 (1990)

Electron spin resonance (ESR) spectra have been obtained for the radical cation of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diamine (TPD) in dichloromethane solution, in solid amorphous films, and in TPD/polycarbonate films doped with tris(p-bromophenyl)ammonium hexachloroantimonate or HNO3.By use of ESR the mediation of electronic charge (hole) transport via the TPD+ radical cation has been observed in the TPD films in the absence of an applied field.Arrhenius activation parameters were calculated for charge transport from the ESR data, giving EA = 10 +/- 2 kJ/mol Α = (1.7 +/- 1) * 1010 s-1, and a rate constant at 300 K of (3.1 +/-1) * 108 s-1.The value of EA is one-half that from time-of-flight (TOF) measurements extrapolated to zero field, while the rate constant is a factor of 10 smaller, and Α is a factor of 1000 smaller.The differences can be understood in terms of the compensation effect due to the presence of residual solvent, and the ion pairing of an TPD+ ions with dopant counterions.In TPD/polycarbonate films the rate of hole transport is too slow to produce significant changes in the ESR spectrum.The rate of charge transport is thus less than 2*108 s-1 in these films, consistent with TOF data.In dichloromethane solution, an EA of 9.8 kJ/mol was observed with ESR.Extrapolating the solution data to solid TPD gives a hole transport rate of 9.75 * 109 s-1, a factor of 3 higher than that from TOF data.The lower Ea and higher rate in dichloromethane solution are consistent with the effect of the higher dielectric constant compared to an TPD film.This suggests that the rate-determing step for hole transport is the same in solution as it is in the solid state.

Electrogenerated chemiluminescence from derivatives of aluminum quinolate and quinacridones: Cross-reactions with triarylamines lead to singlet emission through triplet-triplet annihilation pathways

Gross,Anderson,Slaterbeck,Thayumanavan,Barlow,Zhang,Marder,Hall,Flore Nabor,Wang,Mash,Armstrong,Wightman

, p. 4972 - 4979 (2000)

Solution electrogenerated chemiluminescence (ECL) was evaluated for molecules of interest for organic light-emitting diodes (OLEDs), using high- frequency voltage pulses at a microelectrode Radical cations of different energies were electrogenerated from a series of triarylamine hole-transport materials (x-TPD), in the presence of radical anions of a high electron affinity sulfonamide derivative of tris(8-hydroxyquinoline)aluminum (Al(qs)3), or a bis(isoamyl) derivative of quinacridone (DIQA). The resultant emission was from the excited singlet states 1Al(qs)3* or 1DIQA*, the same excited state produced in OLEDs based on these molecules. In solution, the majority of the reaction pairs had insufficient energy to populate 1Al(qs)3* or 1DIQA* directly, but could form the triplet states 3Al(qs)3* or 3DIQA*. The reaction order and the temporal response of the emission were consistent with subsequent formation of the excited singlet states via triplet-triplet annihilation (TTA). For reactions with a low excess Gibbs free energy to form the triplet state (Δ(T)G), the efficiency increased exponentially with an increase in driving force (increase in oxidation potential of x-TPD), then reached a plateau. At the maximum, the efficiencies for formation of 1Al(qs)3* or 1DIQA* via the TTA route reach as high as a few percent. The computed energetics of these reactions suggest that similar light-producing electroluminescent reactions, proceeding via triplet formation, could also occur in condensed phase organic thin films.

In-situ generation and analysis of charge transfer materials using an OTTLE cell and resonance Raman scattering

Littleford, Rachael E.,Paterson, Michael A. J.,Low, Paul J.,Tackley, Daniel R.,Jayes, Linda,Dent, Geoffrey,Cherryman, Julian C.,Brown, Bev,Smith, W. Ewen

, p. 3257 - 3263 (2004)

Poly(aryl)amine based charge transfer materials (CTMs) are essential components in a range of present and future technologies, from the Xerox process to display devices based upon light emitting polymers (LEPs). However, there is a lack of detailed understanding regarding the electronic properties of CTMs in their various neutral and oxidized forms. This paper reports the use of an optically transparent thin layer electrochemical (OTTLE) cell in combination with a Raman microprobe system and DFT calculations to provide information on the molecular and electronic structure of the mono- and di-oxidized derivatives of the classic CTM N,N′-diphenyl-N,N′-bis(3-methylphenyl)(1, 1′-biphenyl)-4,4′-diamine (TPD) and the closely related species N,N′-diphenyl-N,N′-bis(2,4-dimethylphenyl)(1,1′-biphenyl)-4, 4′-diamine (DMTPD). The resonance Raman scattering profile easily discriminates between the monovalent and divalent cations while DFT calculations permit correlation of the observed vibrational frequencies with localized atomic displacements. The cations are best described in terms of a symmetrical (i.e. fully delocalized) structure. The high sensitivity of the method suggests that it should be appropriate for the observation of low concentrations of the various cations generated from TPD type CTMs during device operation.

Hole Transport in Solid Solutions of a Diamine in Polycarbonate

Stolka, M.,Yanus, J. F.,Pai, D. M.

, p. 4707 - 4714 (1984)

Hole transport has been investigated in films of solutions of N,N'-diphenyl-N,N'-bis(3-methylphenyl)--4,4'-diamine in bisphenol A polycarbonate.Charge carrier mobilities in excess of 1E-3 cm2/(Vs) have been observed at room temperature at electric fields lower than 1E4 V/cm.The values of hole mobility were between 1E-10 and 1E-3 cm2/(Vs) as the molecular concentration was varied from 9 to 100 wtpercent.At high concentrations of the transport molecule and at fields less than 1E5 V/cm, the mobility is essentially independent of electric field.Field dependence was observed at lower concentrations and high fields.

(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination

Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.

, p. 10343 - 10359 (2021/07/31)

(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.

Synthesis of unsymmetrically substituted triarylaminesviaacceptorless dehydrogenative aromatization using a Pd/C andp-toluenesulfonic acid hybrid relay catalyst

Jin, Xiongjie,Koizumi, Yu,Mizuno, Noritaka,Nozaki, Kyoko,Takayama, Satoshi,Yamaguchi, Kazuya,Yatabe, Takafumi

, p. 4074 - 4084 (2020/05/25)

An efficient and convenient procedure for synthesizing triarylamines based on a dehydrogenative aromatization strategy has been developed. A hybrid relay catalyst comprising carbon-supported Pd (Pd/C) andp-toluenesulfonic acid (TsOH) was found to be effective for synthesizing a variety of triarylamines bearing different aryl groups starting from arylamines (diarylamines or anilines), using cyclohexanones as the arylation sources under acceptorless conditions with the release of gaseous H2. The proposed reaction comprises the following relay steps: condensation of arylamines and cyclohexanones to produce imines or enamines, dehydrogenative aromatization of the imines or enamines over Pd nanoparticles (NPs), and elimination of H2from the Pd NPs. In this study, an interesting finding was obtained indicating that TsOH may promote the dehydrogenation.

Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof

-

, (2018/07/30)

The invention relates to a method for preparing a biphenyl triarylated amine compound by taking carboxyl as a guide group, an intermediate and a preparation method thereof. The intermediate has a structure as shown in the formula, (the formula is shown in the description), wherein R is selected from hydrogen, alkyl with a carbon atom number of 1-10, halogenated alkyl with a carbon atom number of 1-5, alkoxy with a carbon atom number of 1-5 and aryl. The intermediate is prepared from simple and easily available raw materials, and the biphenyl triarylated amine compound prepared by the intermediate is high in purity and yield, so that the production cost of the biphenyl triarylated amine compound can be remarkably reduced, and therefore, the method is very suitable for industrial productionof the biphenyl triarylated amine compound.

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

Maddala, Sudhakar,Mallick, Sudesh,Venkatakrishnan, Parthasarathy

, p. 8958 - 8972 (2017/09/11)

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.

Method for producing hydroxytriarylamine (by machine translation)

-

Paragraph 0037, (2018/02/24)

PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT

The heterogeneous catalyst using the same and method of manufacturing hydroxytriarylamine compd. (by machine translation)

-

Paragraph 0089; 0098; 0099, (2016/10/09)

PROBLEM TO BE SOLVED: To provide an industrially-useful heterogeneous catalyst for coupling reaction, and a method for producing a triarylamine compound and/or triarylamine polymer using the heterogeneous catalyst. SOLUTION: The heterogeneous catalyst for coupling reaction includes a carrier, a palladium compound, and tri (tert-butyl) phosphine, and is characterized in that the palladium compound content in weight is 0.03 to 0.2 times the carrier weight in terms of palladium atom and the tri (tert-butyl) phosphine content in mole is 0.6 to 12 times one palladium atom mole in the palladium compound. In addition, the heterogeneous catalyst is used. COPYRIGHT: (C)2013,JPO&INPIT

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