101895-77-6

Basic information

• Product Name: 2,6-bis[(phenylamino)methylene]pyridine
• Synonyms: 2,6-bis[(phenylamino)methylene]pyridine
• CAS NO: 101895-77-6
• Molecular Weight: 285.348
• Mol File: 101895-77-6.mol

Chemical Properties

• CAS DataBase Reference: 2,6-bis[(phenylamino)methylene]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis[(phenylamino)methylene]pyridine(101895-77-6)
• EPA Substance Registry System: 2,6-bis[(phenylamino)methylene]pyridine(101895-77-6)

Safety Data

• Hazardous Substances Data: 101895-77-6(Hazardous Substances Data)

Upstream product

• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 62-53-3 aniline 
• 1195-59-1 2.6-bis(hydroxymethyl)pyridine 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 

Downstream Products

• 1248447-17-7 N,N′-(pyridine-2,6-diylbis(methylene))dianiline 
• 880546-41-8 C₃₈H₃₀N₆Zn⁽²⁺⁾ 
• 1289160-31-1 [2,6-bis(phenylimino)pyridine]cobalt dichloride 

Relevant articles and documents

Recognition between V- and dumbbell-shaped molecules

A series of 2,6-bis(imino)pyridyl-based V-shaped compounds bearing various para-substituents on the terminal aromatic rings [C5H 3N(CHN-C6H4R)2; R = OMe, iPr, Me, H, Cl, F, and CF3] have been prepared and investigated for their reversible binding with the dumbbell-shaped cations NH2+-{CH2-C6H3(OMe-3,5) 2}2 and 9-anthryl-CH2-NH2 +-CH2-C6H3(OMe-3,5)2. Three crystalline V-shaped compounds and a dumbbell hexafluorophosphate were characterised in the solid state by X-ray structural analysis. The binding mode of the 1 : 1 V-shaped molecule·dumbbell complexes was evaluated by 1H NMR spectroscopy. The binding constants (90-400 M-1 in dichloromethane) and stoichiometries of the complexes were determined using the Method of Continuous Variations and the Rose-Drago Method based on 1H NMR spectroscopic data. In a series of V-shaped compounds, the binding strength with both dumbbell cations diminishes with the decreasing electron-donating ability of the R substituents. Specifically, one of the diimine V-shaped compounds shows a stronger binding with the symmetrical dumbbell than with the unsymmetrical anthracene-containing dumbbell. Fluorescence measurements of equimolar mixtures of the V-shaped compounds and the unsymmetrical dumbbell have revealed a reduced anthracene emission which is approximately 50% that of the original intensity. Rapid and complete dissociation (5 min) of the V-shaped compounds from the dumbbells was realised using an excess of acid or base, whereas only partial dissociation of the complexes was achieved with a large excess of water (1 h).

Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents

In this study we synthesized a series of sixteen bis(imino)pyridines (BIPs) starting from 2,6-diaminopyridine and various aromatic aldehydes, and evaluated their antioxidant, antibacterial, antifungal and acetylcholinesterase (AChE) inhibitory activity. T

Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles

Supramolecular polymerization of imine-linked macrocycles has been coupled to dynamic imine bond exchange within a series of macrocycles and oligomers. In this way, macrocycle synthesis is driven by supramolecular assembly, either into small aggregates su

Efficient Pincer-Ruthenium Catalysts for Kharasch Addition of Carbon Tetrachloride to Styrene

A series of NNN pincer-ruthenium complexes (R2NNN)RuCl2(PPh3) (R=Cyclohexyl (Cy), t-butyl (tBu), i-propyl (iPr) and phenyl (Ph)) have been synthesized and characterized. These pincer-ruthenium complexes have been used to catalyse the Kharasch addition or atom transfer radical addition (ATRA) of carbon tetrachloride to styrene. Among the pincer-ruthenium catalysts screened for the Kharasch addition, the catalytic activity followed the order (Cy2NNN)RuCl2(PPh3)>(iPr2NNN)RuCl2(PPh3)?(Ph2NNN)RuCl2(PPh3). The oxidation of Ru(II) is easier with (Cy2NNN)RuCl2(PPh3) and (iPr2NNN)RuCl2(PPh3) in comparison with (Formula presented.) RuCl2(PPh3) as indicated by cyclic voltammetry studies. The catalyst precursor (R2NNN)RuCl2(PPh3) itself is the resting state of the reaction. The rate determining step involves the generation of the five-coordinate 16-electron ruthenium(II) species (R2NNN)RuCl2. Owing to weaker binding of triphenyl phosphine to ruthenium, the generation of catalytically active 16-electron species (Cy2NNN)RuCl2 and (iPr2NNN)RuCl2 are more favourable. The complex (Cy2NNN)RuCl2(PPh3) demonstrates very high productivity (5670 turnovers after 48 h at 140 °C) in the absence of any co-catalyst radical initiator. To the best of our knowledge, our turnovers (ca. 5670) are much higher than that reported hitherto. Quantum mechanical calculations demonstrate that the path involving the activation of carbon tetrachloride by (Cy2NNN)RuCl2 is more favoured than the path where carbon tetrachloride is activated by (Cy2NNN)RuCl2(η2-styrene). Density functional theory (DFT) and kinetic studies are in accord with the widely accepted mechanism involving the single electron transfer (SET) from ruthenium(II) to chloride radical with concomitant generation of a benzyl radical which is trapped by the resulting ruthenium(III) species. (Figure presented.).

Structural, spectral, and photoreactivity properties of mono and polymetallated-2,2′-bipyridine ruthenium(II) complexes

Polymetallated-2,2′-bipyridine–ruthenium(II) complexes exhibit photosensitization properties and can enhance optically induced NO release, thus modeling multi-site catalysts. Two novel ruthenium-nitrosyl complexes [RuCl2LA(NO)]PF6 (herein called RuLANO, LA = 2,6-bis[(aniline)methyl]-pyridine) and [RuCl2(NO)({Ru(bpy)2}2-μ-LB)](PF6)5 (herein called Ru3LBNO, LB = 2,6-bis[(1,10-phenantroline-5-amine)methyl]-pyridine) were prepared and structurally characterized (1H-, 13C-, DEPT-135 NMR, FTIR, UV–Vis, elemental analysis, ESI-HRMS, and single crystal x-ray diffraction). RuLANO showed a trans configuration of the chloride ligands, and photo-release of chloride is the major process upon irradiation of RuLANO at 377 nm, along with some NO dissociation to a small extent. In contrast, the trinuclear ruthenium complex Ru3LBNO was found to be photo-inactive with irradiation between 377 and 447 nm (region of absorption of the {Ru(bpy)2(phen)}2+ chromophore) in the same conditions of RuLANO. This result agrees with the strong stabilization of Rucentral dxy, dxz, and dyz orbitals as shown by calculations using density functional theory (DFT), as well as with the electrochemical response, which supports that there is no major electronic communication between the central and the peripherals ruthenium ions in the trinuclear complex.

Synthesis of pyridine derivatives as potential antagonists of chemokine receptor type 4

A series of pyridine derivatives were synthesized as potential inhibitors of chemokine receptor type 4. This chemokine receptor has been linked to various disease pathways including HIV-1 proliferation, autoimmune disorders, inflammatory diseases, and cancer metastasis. The compounds were tested for activity using an affinity binding assay and an assay that tests the ability to inhibit cell invasion. Two hit compounds (2b and 2j) have been identified for further evaluation that inhibit cell invasion by at least 50% and have an effective concentration of less than 100 nm in the binding affinity assay. The structures of the synthesized compounds were confirmed by spectral data.

Synthesis of bistetrahydroquinolines as potential anticholinesterasic agents by double diels-alder reactions

The tetrahydroquinoline ring system is a unit found in many biologically active natural products and pharmacologically relevant therapeutic agents. A new series of bistetrahydroquinolines (bis-THQs) was synthesized using imino Diels-Alder reactions betwee

Process for oligomerization of ethylene to linear alpha-olefins

A process for preparing α-olefins from ethylene wherein the α-olefins are substantially free of olefins having greater than 12 carbon atoms comprises contacting ethylene under oligomerization conditions with a 2,6-bis(phenylimino) pyridyl metal halide cat

Molecular architecture. 1. Sodium, potassium, and strontium complexes of a hexaazamacrocycle, an 18-crown-6/torand analogue

Complexes of 4,5:15,16-dibenzo-3,6,14,17,23,24-hexaazatricyclo[17.3.1.1 8,12]tetracosa-1(23),4,8-(24),9,11,15,19,21-octaene (2) with Sr(CF3SO3)2 and SrI2 have been prepared by templated 2 + 2 cyclocon