2847-14-5

Basic information

• Product Name: N,N'-bis(2-pyridylmethylene)ethylenediamine
• Synonyms: N,N'-bis(2-pyridylmethylene)ethylenediamine;2,2-Ethylene bisnitrilomethylidene dipridine;1,2-Bis(2-pyridinylmethyleneamino)ethane;2,2'-[Ethylenebis(nitrilomethylidyne)]bispyridine;N,N'-Bis(2-pyridylmethylene)-1,2-ethanediamine;N,N'-Bis(pyridin-2-ylmethylene)-1,2-ethanediamine;N,N'-Ethylenebis(pyridine-2-methanimine);Einecs 220-649-5
• CAS NO: 2847-14-5
• Molecular Formula: C₁₄H₁₄N₄
• Molecular Weight: 238.28776
• EINECS: 220-649-5
• Mol File: 2847-14-5.mol
• Article Data: 38

Chemical Properties

• Melting Point: 64-65.5 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 415.2°Cat760mmHg
• Flash Point: 204.9°C
• Appearance: /
• Density: 1.08g/cm³
• PKA: 4.66±0.50(Predicted)
• CAS DataBase Reference: N,N'-bis(2-pyridylmethylene)ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis(2-pyridylmethylene)ethylenediamine(2847-14-5)
• EPA Substance Registry System: N,N'-bis(2-pyridylmethylene)ethylenediamine(2847-14-5)

Safety Data

• Hazardous Substances Data: 2847-14-5(Hazardous Substances Data)

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 107-15-3 ethylenediamine 

Downstream Products

• 1426946-32-8 N¹,N²-bis(4-chlorobenzyl)-N¹,N²-bis(pyridin-2-ylmethyl)ethane-1,2-diamine 
• 1363649-73-3 N⁽¹⁾,N⁽²⁾-diphenyl-N⁽¹⁾,N⁽²⁾-di(pyrido[1,2-a]indol-10-yl)ethane-1,2-diamine 
• 140-28-3 N,N'-Dibenzylethylenediamine 
• 884482-55-7 [Cu₂(1,2-bis(2'-pyridylmethyleneamino)ethane)(PPh₃)2I₂] 
• 882522-33-0 3,3'-(ethane-1,2-diyl)bis(2-(pyridin-2-yl)thiazolidin-4-one) 
• 4608-34-8 N,N'-bis(2-pyridylmethyl)ethylenediamine 

Relevant articles and documents

Copper(II) Schiff base complexes and their mixed thin layers with ZnO nanoparticles

Cu(II) complexes with Schiff bases derived from ethylenediamine (en) and 2-pyridinecarboxaldehyde (pyca), 2,5-dimethoxybenzaldehyde (dmbaH) or 4-imidazolecarboxaldehyde (4Him) were obtained and studied by elemental analysis, UV-VIS and IR spectra. Zinc oxide was synthesized using a simple homogeneous precipitation method with zinc acetate as a starting material. Thin layers of the studied Cu(II) complexes were deposited on Si(111) or ZnO/Si(111) substrates by a spin coating method and characterized with a scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM) and fluorescence spectroscopy. For Cu(II) layers the most intensive fluorescence bands due to intra-ligand transitions were observed between 462 and 503 nm. The fluorescence intensity of thin layers was corelated to the rotation speed. In the case of the [Cu(II)(en(4Him)2)Cl2](2a)/ZnO/Si and [Cu(en(dmbaH)2)Cl2](3a)/ZnO/Si layers the quenching of the emission band from ZnO at 440 nm (λex = 330 nm) associated with various intrinsic or extrinsic lattice defects was noted. [Figure not available: see fulltext.]

Synthesis of three new branched octadentate (N8) Schiff Base and competitive Lithium-7 NMR study of the stoichiometry and stability constant of Mn2+, Zn2+ and Cd2+ complexes in acetonitrile – [(BMIM)(PF6)] mixture

Three new branched hexadentate amines, have been synthesized. Condensation with picolinaldehyde in methanol leads to produce three new Schiff base, with two 2-pyridylmethyl pendant arms. 7Li NMR spectroscopy was used to investigation the stability and stoichiometry information of a Li+ complex with three symmetrical branched Schiff base (Sc.B.1), (Sc.B.2) and (Sc.B.3) in 0–100, 25–75, 50-50 and 75–25 w/w% acetonitrile – [(BMIM)(PF6)] ionic liquid mixture solution. A competitive 7Li NMR manner was also used to probe the complexation of Schiff bases with Mn2+, Zn2+ and Cd2+ ions in the same solvent systems. The stability constants of the resulting complexes were estimated from computer fitting of the mole ratio information to an equation that relates the observed chemical shifts to the stable constant. There is a reverse relevance of the complex stability and the amount of ionic liquid in the solvent mixture. In of the all experimented solvent mixture, the stability of the resulted 1:1 complexes were found to change in the order M-Sc.B.1>M-Sc.B.2>M-Sc.B.3 and Cd2+> Mn2+> Zn2+.

Synthesis and structures of two cobalt(III) complexes with N4 donor ligands: Isolation of a unique bis-hemiaminal ether ligand as the metal complex

Two cobalt(III) complexes, [CoL1(N3) 2]ClO4·H2O (1) and [CoL 2(N3)2]NO3 (2), where L1 = N,N′-bis-(2-pyridylmethyl)-1,2-ethanediamine, L2 = N,N′-bis-(1-methoxy-1-pyridin-2-yl-methyl)-ethane-1,2-diamine and both ligands are tetradentate N4 donors, have been prepared and characterized by elemental analysis, IR and UV-Vis spectroscopy, cyclic voltammetry and single crystal X-ray diffraction studies. Both compounds assume an asymmetric cis-octahedral (N2/N2) geometry. Complex 1 crystallizes in the orthorhombic space group Pbca with cell dimensions a = 9.7593(2) A?, b = 16.8640(3) A?, c = 25.8206(5) A?, Z = 8, whereas complex 2 crystallizes in the monoclinic space group P21/c with cell dimensions a = 14.437(3) A?, b = 15.596(3) A?, c = 19.187(3) A?, β = 93.642(2), Z = 8. In complex 2, a new bis-hemiaminal ether ligand was found to be "trapped". Hemiaminal ethers are known to be very unstable intermediates and no crystal structure of any bis-hemiaminal ether has been reported to date. Complex 2 represents a uniquely stable system containing the trapped bis-hemiaminal ether L2.

Peroxide-Templated Assembly of a Trimetal Neodymium Complex Single-Molecule Magnet

In this work, we present a trimetal neodymium complex with two notable qualities. First, the assembly of the complex is templated by peroxide derived from atmospheric oxygen. Second, the bulk material behaves as a superparamagnet, implying that the individual complexes are molecular magnets. Peroxide-templated assembly is possible because of the confluence of the high oxophilicity of neodymium along with the use of an azeotropic distillation synthesis method, which excludes water but admits oxygen. SQUID magnetometry measurements show an extremely high magnetic susceptibility as well as a lack of remanence.

Synthesis, characterization and DNA interaction of copper (II) complexes with Schiff base ligands derived from 2-pyridinecarboxaldehyde and polyamines

A series of copper (II) complexes a-d with Schiff bases ligands derived from the condensation reactions between 2-pyridinecarboxaldehyde and different polyamines (ethylenediamine, diethylenetriamine, triethylenetetramine and tetraethylenepentamine) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, HRMS, molar conductance and molecular modeling studies. The interactions of the copper complexes a-d with DNA were investigated by the UV spectra, viscosity measurements and gel electrophoresis under physiological conditions. The experimental results indicated that four complexes could bind to DNA via an intercalative mode and showed a different DNA cleavage activity with the sequence: d > c > a > b.

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Complexation studies of Mn2+, Zn2+ and Cd 2+ ions with a series of tetradentate (N4) Schiff base ligands containing pyridine moiety in acetonitrile and nitromethane solutions by a competitive NMR technique using 7Li nucleus as a probe

Lithium-7 NMR spectroscopy was used to investigate the stoichiometry and stability of a Li+ complex with N1,N2- bis(pyridin-2-ylmethylene)ethane-1,2-diamine (L1), N 1,N3-bis(pyridin-2-ylmethylene)propane-1,3-diamine (L 2) and N1,N4-bis(pyridin-2-ylmethylene) butane-1,4-diamine (L3) in acetonitrile (AN) and nitromethane (NM) solutions. A competitive 7Li NMR method was also employed to probe the complexation of Mn2+, Cd2+ and Zn2+ ions with L1, L2 and L3 in the same solvents. The formation constants of the resulting complexes were evaluated from computer fitting of the mole ratio data to an equation that relates the observed chemical shifts to the formation constant. In both solvents, the stability of the resulting 1:1 complexes were found to vary in the order Zn2+> Cd2+>Mn2+>Li+. In addition, the stability of M-L complexes of M2+ with the Schiff base ligands found to vary in the order M2+-L1 > M2+-L2 > M2+-L3.

Design, synthesis and biological evaluation of Schiff’s base derivatives as multifunctional agents for the treatment of Alzheimer’s disease

A series of Schiff’s base derivatives was rationally designed, synthesized, and evaluated as multi-function agents for the treatment of Alzheimer’s disease (AD). The results revealed that compound 3b was a novel multifunctional agent. It acted as a highly selective monoamine oxidase-B inhibitor (IC50 = 8.4 nM), which was explained by the docking study. Compound 3b also was an antioxidant agent (2.3 eq) and could significantly inhibit self-induced Aβ1-42 aggregation (31.8%). Meanwhile, compound 3b was a selective metal chelator and could inhibit Cu2+-induced Aβ1-42 aggregation (62.3%). Furthermore, compound 3b presented good neuroprotective effects on H2O2-induced PC12 cell injury. More importantly, compound demonstrated good blood brain barrier permeability and druglike properties. Therefore, compound 3b, a promising multi-targeted active molecule, offers an attractive starting point for further study in the drug-discovery process against AD.[Figure not available: see fulltext.].

Synthesis of novel benzimidazoles and benzothiazoles via furan-2-carboxaldehydes, o-phenylenediamines, and 2-aminothiophenol using Cu(II) Schiff-base@SiO2 as a nanocatalyst

2-(5-Substituted phenyl)furan-2-carboxaldehyde derivatives were prepared by using an efficient copper(II) complex of tetradentate Schiff-base ligand immobilized onto silica as a heterogeneous nanocatalyst [Cu(II) Schiff-base@SiO2] (5.0?mol%) using anilines, sodium nitrite, and furan-2-carboxaldehyde. Furthermore, attractive di-heteroaryl benzo-fused systems such as benzimidazole and benzothiazole derivatives were synthesized using this nanocatalyst (5.0?mol%) via the reaction of o-phenylenediamines and 2-aminothiophenol with 2-(5-substituted phenyl)furan-2-carboxaldehydes in EtOH. The catalyst was characterized by Fourier transform infrared (FT-IR), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDX), X-ray powder diffraction (XRD), and inductively coupled plasma (ICP) techniques. The advantages of the present catalytic system are short reaction times, mild conditions, good to excellent yields, and low amount of nanocatalyst. Moreover, to the best of our knowledge, this is the first time of using the same catalyst in two steps including synthesis of 2-(5-substituted phenyl)furan-2-carboxaldehyde and benzimidazole or benzothiazole derivatives. In addition, the synthesized catalyst was recycled very well and reused several times without significant loss of its catalytic activity.