2879-66-5

Basic information

• Product Name: N,N'-Diphenyl-1,2-diphenylethane-1,2-diamine
• Synonyms: 1,2,N,N'-Tetraphenyl-1,2-ethanediamine;N,N',1,2-Tetraphenyl-1,2-ethanediamine;N,N',1,2-Tetraphenylethane-1,2-diamine;N,N'-Diphenyl-1,2-diphenylethane-1,2-diamine;N,N'-Diphenyl-α,β-bibenzyldiamine;α,β-Bisanilinobibenzyl
• CAS NO: 2879-66-5
• Molecular Formula: C₂₆H₂₄N₂
• Molecular Weight: 364.48216
• Mol File: 2879-66-5.mol
• Article Data: 57

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N'-Diphenyl-1,2-diphenylethane-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diphenyl-1,2-diphenylethane-1,2-diamine(2879-66-5)
• EPA Substance Registry System: N,N'-Diphenyl-1,2-diphenylethane-1,2-diamine(2879-66-5)

Safety Data

• Hazardous Substances Data: 2879-66-5(Hazardous Substances Data)

Upstream product

• 4553-59-7 2-anilino-2-phenylacetonitrile 
• 925-90-6 ethylmagnesium bromide 
• 67-56-1 methanol 
• 139212-76-3 methyl trans-3-(p-methoxyphenyl)-5-(trans-1,3,4,5-tetraphenylperhydro-2-imidazolyl)-2-isoxazoline-4-carboxylate 
• 151257-56-6 1,2-Bis-benzotriazol-1-yl-N,N'-diphenyl-ethane-1,2-diamine 
• 75-77-4 chloro-trimethyl-silane 
• 538-51-2 benzylidene phenylamine 
• 75-00-3 chloroethane 
• 124-38-9 carbon dioxide 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 95-14-7 1,2,3-Benzotriazole 
• 91-01-0 1,1-Diphenylmethanol 
• 67-64-1 acetone 
• 1137-96-8 N-(benzylidene)aniline N-oxide 

Downstream Products

• 2879-66-5 (+)-N,N'-diphenyl-bibenzyl-α,α'-diyldiamine 
• 60644-40-8 1,3-cis-4,5-Tetraphenyl-imidazolidin 
• 60644-40-8 (4S,5S)-1,3,4,5-Tetraphenyl-imidazolidine 
• 135075-62-6 (4RS,5RS)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 135075-66-0 (2S,3S,4S,5R)-5-Phenyl-3-((4R,5R)-1,3,4,5-tetraphenyl-imidazolidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester 
• 135075-66-0 (2S,3S,4S,5R)-5-Phenyl-3-((4S,5S)-1,3,4,5-tetraphenyl-imidazolidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester 

Relevant articles and documents

A Metal-Free Approach to 1,2-Diamines via Visible Light-Driven Reductive Coupling of Imines with Perylene as a Photoredox Catalyst

A simple, metal-free, and versatile approach to 1,2-diamines has been developed based on reductive coupling reactions of various imines, where perylene, an aromatic hydrocarbon, was used as a photoredox catalyst under visible light irradiation using a white light-emitting diode. The use of 1 mol % perylene enabled almost complete conversion of the imines, leading to the formation of their corresponding 1,2-diamines, which were isolated in good yields. The ratios between dl and meso diamines ranged from 31:69 to 82:18 depending on the substituents of the imines.

Titanium promoted reduction of imines with Grignards, silanes, and zinc: Identification of a new mechanism with silanes

Aldimines react with reducing agents, such as Grignards, phenylsilane or zinc in the presence of titanium(IV) isopropoxide to form amines and reductively coupled imines (diamines). Using deuterium labeled reagents, the mechanism of reduction to form amine

Computational tools for mechanistic discrimination in the reductive and metathesis coupling reactions mediated by titanium(IV) isopropoxide

A theoretical study has been carried out at the B3LYP/LANL2DZ level to compare the reactivity of phenyl isocyanate and phenyl isothiocyanate towards titanium(IV) alkoxides. Isocyanates are shown to favour both mono insertion and double insertion reactions. Double insertion in a head-to-tail fashion is shown to be more exothermic than double insertion in a head-to-head fashion. The head-to-head double insertion leads to the metathesis product, a carbodiimide, after the extrusion of carbon dioxide. In the case of phenyl isothiocyanate, calculations favour the formation of only mono insertion products. Formation of a double insertion product is highly unfavourable. Further, these studies indicate that the reverse reaction involving the metathesis of N,N ′-diphenyl carbodiimide with carbon dioxide is likely to proceed more efficiently than the metathesis reaction with carbon disulphide. This is in excellent agreement with experimental results as metathesis with carbon disulphide fails to occur. In a second study, multilayer MM/QM calculations are carried out on intermediates generated from reduction of titanium(IV) alkoxides to investigate the effect of alkoxy bridging on the reactivity of multinuclear Ti species. Bimolecular coupling of imines initiated by Ti(III) species leads to a mixture of diastereomers and not diastereoselective coupling of the imine. However if the reaction is carried out by a trimeric biradical species, diastereoselective coupling of the imine is predicted. The presence of alkoxy bridges greatly favours the formation of the d,l (±) isomer, whereas the intermediate without alkoxy bridges favours the more stable meso isomer. As a bridged trimeric species, stabilized by bridging alkoxy groups, correctly explains the diastereoselective reaction, it is the most likely intermediate in the reaction.