51927-78-7

Basic information

• Product Name: N,N′-diphenyl-(1,1′-binaphthyl)-4,4′-diamine
• Synonyms: N,N′-diphenyl-(1,1′-binaphthyl)-4,4′-diamine
• CAS NO: 51927-78-7
• Molecular Weight: 436.556
• Mol File: 51927-78-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: N,N′-diphenyl-(1,1′-binaphthyl)-4,4′-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N′-diphenyl-(1,1′-binaphthyl)-4,4′-diamine(51927-78-7)
• EPA Substance Registry System: N,N′-diphenyl-(1,1′-binaphthyl)-4,4′-diamine(51927-78-7)

Safety Data

• Hazardous Substances Data: 51927-78-7(Hazardous Substances Data)

Upstream product

• 62012-57-1 4,4'-diiodo-1,1'-binaphthalene 
• 62-53-3 aniline 
• 90-13-1 1-Chloronaphthalene 
• 90-30-2 N-phenyl-1-naphthylamine 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 851767-84-5 C₆₄H₄₀N₂ 
• 89444-23-5 4,4'-bis(N-phenyl-N-acetylamino)-1,1'-binaphthyl 

Relevant articles and documents

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.

Iron(III)-promoted oxidative coupling of naphthylamines: Synthetic and mechanistic investigations

A facile route to the synthesis of 1,1′-binaphthyl-4,4′- diamines (naphthidines) and 1,1′-binaphthyl-2,2′-diamines (BINAMs) was developed by the oxidative homocoupling of 1- and 2-naphthylamines, respectively, using FeCl3 as oxidant and K2CO3 as base in 1,2-dichloroethane under ambient conditions. A preliminary mechanistic investigation was performed by the ESR spectroscopy and intermediate-trapping technique.

Facile synthesis and characterization of naphthidines as a new class of highly nonplanar electron donors giving robust radical cations

Naphthidines 2 were prepared by nickel-catalyzed amination of 1-chloronaphthalene followed by oxidative homocoupling of 1-naphthalene amines 1 using titanium(IV) tetrachloride. The electronic and magnetic properties of materials 2 were investigated by cyclic voltammetry and other electrochemical techniques, EPR and UV-visible spectroscopies, and magnetic susceptibility. It was demonstrated that compounds 2 could be easily and reversibly oxidized via a two-electron-transfer reaction into their bis(radical cation) 22.2+, which displays a substantial stability at room temperature (the half-life of 22.2+ estimated by EPR at 25 °C was 10 days). B3LYP/6-31G* optimized structures of N,N′-bis(4-methoxyphenyl)-(1,1′-binaphthyl)- 4,4′-diamine 2g shows significant differences in the torsion angle between the naphthalene moieties depending on its oxidation state. Twisted structures are preferred for neutral compounds, whereas more planar are favored for the oxidized forms 2g+ and 2g2.2+ to realize spin and/or charge delocalizations over the whole π-system. Such conformation changes concerted with the electron transfers contribute to explain the unusual two-electron process observed in the electrochemical behavior of 2g instead of the two single-electron transfers that would have been expected in the case of two successive oxidations. It is finally shown that the oxidation of 2g in CH2Cl2 with thianthrenium perchlorate (ThClO4) generates the dication 2g2.2+ with singlet spin-multiplicity.