76185-65-4

Basic information

• Product Name: N,N,N',N'-Tetrakis(4-methylphenyl)-benzidine
• Synonyms: 1,1'-Biphenyl]-4,4'-diaMine,N4,N4,N4',N4'-tetrakis(4-Methylphenyl)-;N4,N4,N4',N4'-Tetra-p-tolyl-[1,1'-biphenyl]-4,4'-diaMine;TP-TPD;TM-TPB;N,N,N',N'-Tetrakis(p-tolyl)benzidine (purified by sublimation);TMTPD;N,N,N',N'-Tetrakis(p-tolyl)benzidine;N,N,N',N'-Tetrakis(p-tolyl)benzidine (purified by sublimation)
• CAS NO: 76185-65-4
• Molecular Formula: C₄₀H₃₆N₂
• Molecular Weight: 544.73
• EINECS: 1533716-785-6
• Product Categories: OLED;electronic;Electronic Chemicals;Electroluminescence;Functional Materials;Pale-White Powder
• Mol File: 76185-65-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 218 °C
• Boiling Point: 701.741 °C at 760 mmHg
• Flash Point: 310.749 °C
• Appearance: /
• Density: 1.13 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Tetrahydrofuran
• PKA: -1.70±0.60(Predicted)
• CAS DataBase Reference: N,N,N',N'-Tetrakis(4-methylphenyl)-benzidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetrakis(4-methylphenyl)-benzidine(76185-65-4)
• EPA Substance Registry System: N,N,N',N'-Tetrakis(4-methylphenyl)-benzidine(76185-65-4)

Safety Data

• Hazardous Substances Data: 76185-65-4(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow solid

Upstream product

• 3001-15-8 4,4'-diiodobiphenyl 
• 620-93-9 di-p-tolylamine 
• 58047-42-0 4-bromo-N,N-di-p-tolylaniline 
• 106-38-7 para-bromotoluene 
• 92-87-5 p,p'-diaminobiphenyl 
• 106-43-4 para-chlorotoluene 
• 75752-15-7 4,4'-diaminobiphenyl hydrochloride 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 20440-95-3 N-phenyl-di-p-tolylamine 

Relevant articles and documents

The molecular structures and electrochemical response of "twisted" tetra(aryl)benzidenes

The compounds N,N,N′,N′-tetra(4-methylphenyl)-(1,1′- biphenyl)-4,4′-diamine (4), N,N,N′,N′-tetra(4-methylphenyl)- (2,2′-dimethyl)-(1,1′-biphenyl)-4,4′-diamine (5a) and N,N,N′,N′-tetra(4-methylphenyl)-(2,2′,6,6′-tetramethyl) -(1,1′-biphenyl)-4,4′-diamine (

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.

Oxidative Dimerization of Triarylamines Promoted by WCl6, Including the Solid State Isolation and the Crystallographic Characterization of a Triphenylammonium Salt

The triphenylammonium salt [NHPh3][WCl6], 1, and the product of the C-C dimerization of triphenylamine, Ph2N(C6H4)2NPh2, 2, were afforded from the reaction between WCl6 and NPh3 in CH2Cl2. Compound 2 was isolated in 43% yield upon hydrolysis of the reaction mixture. The X-ray structure of 1 provides the first crystallographic characterization of the triphenylammonium ion. Combined EPR and DFT studies gave insight into the reaction mechanism, and allowed the identification of WCl5···[Cl(C6H4)NPh2] as a presumable key intermediate. The reactions of WCl6 with 4-bromotriphenylamine, 4,4′-dimethyltriphenylamine, 9-phenylcarbazole, followed by hydrolytic treatment, led to the dimerization products 3-6, in admixture with variable amounts of the parent amines. N,N,N′,N′-tetrakis(4-bromophenyl)-[1,1′-biphenyl]-4,4′-diamine, 3, was isolated in 60% yield from the reaction of WCl6 with 4,4′-dibromotriphenylamine.