10368-25-9

Basic information

• Product Name: N,N'-DIBENZYL-P-PHENYLENEDIAMINE
• Synonyms: N,N'-DIBENZYL-P-PHENYLENEDIAMINE;N,N'-bis(phenylmethyl)benzene-1,4-diamine;N,N''-DIBENZYLBENZENE-1,4-DIAMINE;N,N'-Dibenzyl-1,4-benzenediamine;N,N'-Dibenzyl-1,4-phenylenediamine;Einecs 233-809-4;N(1),N(4)-dibenzyl-1,4-benzenediamine
• CAS NO: 10368-25-9
• Molecular Formula: C₂₀H₂₀N₂
• Molecular Weight: 288.39
• EINECS: 233-809-4
• Mol File: 10368-25-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 462.6°Cat760mmHg
• Flash Point: 290.3°C
• Appearance: /
• Density: 1.154g/cm³
• CAS DataBase Reference: N,N'-DIBENZYL-P-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIBENZYL-P-PHENYLENEDIAMINE(10368-25-9)
• EPA Substance Registry System: N,N'-DIBENZYL-P-PHENYLENEDIAMINE(10368-25-9)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 10368-25-9(Hazardous Substances Data)

Usage

General Description

N,N'-Dibenzyl-p-phenylenediamine is a chemical compound often used as an antioxidant in rubber and plastic products. It works by scavenging and neutralizing free radicals, which helps to prevent degradation and deterioration of materials. N,N'-DIBENZYL-P-PHENYLENEDIAMINE also has some applications in the production of hair dyes and as a reagent in organic synthesis. However, exposure to N,N'-Dibenzyl-p-phenylenediamine has been associated with skin and eye irritation, and it has been classified as a potential human carcinogen. As a result, proper safety precautions should be taken when handling this chemical.

Upstream product

• 106-50-3 1,4-phenylenediamine 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 100-01-6 4-nitro-aniline 
• 61990-58-7 (1E,1′E)-N,N′-(1,4-phenylene)bis(1-phenylmethanimine) 
• 797-20-6 N,N'-dibenzylidene-benzene-1,4-diamine 

Downstream Products

• 63760-12-3 N,N'-dibenzyl-N,N'-p-phenylene-bis-acetamide 
• 477960-55-7 1,3-dibenzyl-3-(4-benzylamino-phenyl)-1-{4-[1,3-dibenzyl-3-(4-benzylamino-phenyl)-ureido]-phenyl}-urea 

Relevant articles and documents

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Synthesis and spectral studies on NiS4, NiS2PN, NiS2P2 chromophores: Single-crystal X-ray structure of [Ni(dbpdtc)2] (dbpdtc = benzyl(4-(benzylamino)phenyl)dithiocarbamate)

Three complexes of a dithiocarbamate ligand (dbpdtc = benzyl(4- (benzylamino)phenyl)dithiocarbamate), namely [Ni(dbpdtc)2] (1), [Ni(dbpdtc)(NCS)(PPh3)] (2) and [Ni(dbpdtc)(PPh3) 2]ClO4 (3) have been prepared. The complexes were characterized by IR, electronic spectroscopy and cyclic voltammetry. A single-crystal X-ray structural analysis was carried out for complex 1 and showed that the nickel is in a distorted square planar environment with a NiS4 chromophore. For the two mixed ligand complexes, the thioureide ν C-N values were shifted to higher wavenumbers compared to [Ni(dbpdtc)2], suggesting increased strength of the thioureide bond due to the presence of the π-accepting phosphine. Electronic spectral studies suggest square planar geometries for the complexes. Cyclic voltammetry showed easier reduction of nickel(II) to nickel(I) in the mixed ligand complexes compared to [Ni(dbpdtc)2].

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

Phosphine-Free Well-Defined Mn(I) Complex-Catalyzed Synthesis of Amine, Imine, and 2,3-Dihydro-1 H-perimidine via Hydrogen Autotransfer or Acceptorless Dehydrogenative Coupling of Amine and Alcohol

The application of nontoxic, earth-abundant transition metals in place of costly noble metals is a paramount goal in catalysis and is especially interesting if the air- and moisture-stable ligand scaffold is used. Herein, we report the synthesis of amines/imines directly from alcohol and amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines and amines can be obtained from the same set of alcohols and amines using the same catalyst, only by tuning the reaction conditions. The amount and nature of the base are found to be a highly important aspect for the observed selectivity. Both the primary and secondary amines have been employed as substrates for the N-alkylation reaction. As a highlight, we showed the chemoselective synthesis of resveratrol derivatives. Furthermore, the Mn-catalyzed dehydrogenative synthesis of structurally important 2,3-dihydro-1H-perimidines has also been demonstrated. Density functional theory calculations were also carried out to model the reaction path and to calculate the reaction profile.

Ti?Pd Alloys as Heterogeneous Catalysts for the Hydrogen Autotransfer Reaction and Catalytic Improvement by Hydrogenation Effects

Ti?Pd alloys were investigated as heterogeneous catalysts for hydrogen autotransfer reactions. This is the first reported study of alloys as catalysts for hydrogen-borrowing reactions using alcohols. We improved the catalytic activities of alloys by increasing their specific surface areas via a hydrogenation?powdering process. The reactivities and selectivities of hydrogenated Ti?Pd alloys [Ti?Pd(Hy)] were higher than those of non-hydrogenated alloy catalysts in N-alkylation by hydrogen autotransfer using alcohols. A plausible catalytic cycle is proposed based on control studies and deuterium labelling experiments.