1762-36-3

Usage

Uses

Used in Catalysis:
Diethyl [2,2'-bipyridine]-3,3'-dicarboxylate is utilized as a ligand in the development of catalytic systems. Its ability to chelate metal ions contributes to the formation of active and selective catalysts, which are crucial for various chemical transformations.
Used in Material Science:
In the field of material science, diethyl [2,2'-bipyridine]-3,3'-dicarboxylate is employed as a component in the synthesis of metal-organic frameworks (MOFs) and other coordination polymers. These materials possess tailored properties, such as porosity, stability, and responsiveness, making them suitable for applications like gas storage, separation, and sensing.
Used in Medicinal Chemistry:
Diethyl [2,2'-bipyridine]-3,3'-dicarboxylate is used as a ligand in the design and synthesis of metal-based pharmaceuticals. The complexes formed can exhibit biological activity, such as antimicrobial, anticancer, or antiviral properties, due to the unique coordination environments and electronic properties imparted by the ligand.
Used in Coordination Chemistry Research:
As a bipyridine derivative, diethyl [2,2'-bipyridine]-3,3'-dicarboxylate is a subject of interest in coordination chemistry research. It is used to explore the fundamental aspects of metal-ligand interactions, coordination geometries, and electronic structures, which are essential for understanding and advancing the field.

Upstream product

• 64-17-5 ethanol 
• 173032-82-1 2,2'-bipyridine-3,3'-dicarboxylic dichloride 
• 4433-01-6 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine 

Relevant academic research and scientific papers

A new dioxotetraamine ligand derived from binicotinic acid: Synthesis, coordination, and fluorescence behaviour towards divalent transition metal ions

A novel bipyridyl-based fluorescent system, N,N'-bis(2-aminoethyl)-2,2'- bipyridine-3,3'-dicarboxamide (BABD), with two different coordination sites, bidentate bipyridyl and tetradentate dioxotetraamine, has been synthesized, and characterized by elemental analysis and spectroscopic (UV-Vis, IR, : 1H NMR, and 13CNMR) methods. The lowest energy molecular geometry of BABD was obtained by empirical then quantum mechanical treatment. The binding ability of BABD with H+, Co(II), Ni(II), Cu(II), and Zn(II) ions was investigated in aqueous 0.1 M KCl at 25 ± 1 °C by potentiometric methods. Four protonation constants were determined for BABD, and were used as input data to evaluate the formation constants of the metal complexes. The coordination behaviour of BABD in solution indicated that at low pH the bipyridyl unit coordinates to all metal ions, but at higher pH (>7.0) coordination of the dioxotetraamine unit occurs with the Cu(II) and Ni(II) ions only. The 3D-model structure of the metal complex was predicted by semi-empirical calculation using the AM1/d Hamiltonian. Fluorimetric titrations indicate that at pH 9 BABD exhibits fluorescence enhancement with increasing concentration of Cu(II) and Ni(II) ions, but at pH 7.2 fluorescence enhancement is observed only in the presence of Cu(II) ions. No remarkable effect on the fluorescence of BABD was observed in the presence of other biologically relevant metal ions, for example Ni(II), Fe(II), Mn(II), Co(II), Zn(II), Mg(II), Ca(II), and Hg(II). Springer-Verlag 2009.

Spectroscopic, electrochemical and computational study of Pt-diimine-dithiolene complexes: Rationalising the properties of solar cell dyes

A series of [Pt(ii)(diimine)(dithiolate)] complexes of general formula [Pt{X,X′-(CO2R)2-bpy}(mnt)] (where X = 3, 4 or 5; R = H or Et, bpy = 2,2′-bipyridyl and mnt = maleonitriledithiolate), have been spectroscopically, electrochemically and computationally characterised and compared with the precursors [Pt{X,X′-(CO2R) 2-bpy}Cl2] and X,X′-(CO2R) 2-bpy. The study includes cyclic voltammetry, in situ EPR spectroelectrochemical studies of fluid solution and frozen solution samples, UV/Vis/NIR spectroelectrochemistry, hyrid DFT and TD-DFT calculations. The effect of changing the position of the bpy substituents from 3,3′ to 4,4′ and 5,5′ is discussed with reference to electronic changes seen within the different members of the family of molecules. The performance of the mnt complexes in dye-sensitised solar cells has been previously described and the superior performance of [Pt{3,3′-(CO2R)2-bpy} (mnt)] is now explained in terms of decreased electronic delocalisation through twisting of the bipyridyl ligand as supported by the EPR and computational results.

Novel trichloroindolizine derivatives via intramolecular acylation of a bis(chloroacyl)bipyridine

3,3′-Bis(alkyloxycarbonyl)-2,2′-bipyridines are produced from the reaction of alcohols with 3,3′-bis(chlorocarbonyl)-2,2′-bipyridine which is generated from the corresponding dicarboxylic acid and thionyl chloride. When the dicarboxylic acid is reacted with a SOCl2-Cl2 mixture, significant amounts of trichloroindolizines are produced. This reaction is likely to take place via initial intramolecular N-chloroacylation of bipyridine 3.

Novel cytotoxic oxopyridoindolizines: Isopropyl-7,8,9-trichloro-6,7,8,9- tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)

A series of eight new alkyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5- oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC), analogues of camptothecin (CPT), were prepared in a one-pot reaction of 2,2′-bipyridine-3,3′- dicarboxylic acid (BPA) with a mixture of thionyl chloride/chlorine, followed by addition of the appropriate alcohol. This led to a mixture of OPIC compounds 3a-d, 4a-d and 3,3′-dialkoxycarbonyl-2,2′-bipyridines (BPE, 2a-d). The isopropyl OPIC 3c and its corresponding diastereoisomer 4c showed marked activity against three cancer cell lines compared to other analogs. These same diastereoisomers also displayed high cytotoxic activity against five leukemia cell lines, thus the presence of an isopropyl substituent on the carboxylic ester, as opposed to other alkyl substituents, appears to play a key role in the cytotoxic potency of this new class of compounds.

Crystal structure of antitubercular complex: Cis-(chloro)-[N,N'-bis- (diethyl-2,2'-bipyridine-3,3'-dicarboxylate)]ruthenium(II) Monohydrate

Diethyl-2,2'-bipyridine-3,3'-dicarboxylate (3 or L) reacts with RuCl 3 ? 3H2O to give cis-(Cl)-[Ru(L)2Cl 2] ? H2O (4) and structure of the complex was determined by spectral (IR, 1H-NMR), and mass spectroscopic data, elemental analyses and X-ray crystallography. The structure is solved in triclinic, space group p-1 with a = 10.658 (2), b = 12.446 (3), c = 14.186 (5) A, α = 104.856 (3), β = 108.704 (3), γ = 94.973 (2)°, V = 1693.2 (8) A3, Z = 2 with final R = 0.012. The geometry of the complex is shown to be a distorted octahedral with four nitrogens of two 2,2'-bipyridyl ligands in two different planes with Ru-N distance as 2.021 (2)-2.071 (3) A. The cis-position is occupied by two chloride atoms with Ru-Cl distance as 2.4156 (12) and 2.4167 (13) A. The trans-axial Cl2-Ru1-N and Cl1-Ru1-N4 angles are respectively, 172.42 (7) and 174.12 (7)°. A weak hydrogen bonding is observed between the two chlorides and hydrogens of neighbouring molecule [C-H???Cl distance as 2.72, 2.77 (4) A]. A second type of weak hydrogen bonding is also observed between the oxygens of carboxylate groups and hydrogens of a neighbouring molecule [C-H???O distance as 2.53, 2.56 and 2.34 (4) A].