1762-46-5

Basic information

• Product Name: diethyl 2,2'-bipyridine-5,5'-dicarboxylate
• Synonyms: diethyl 2,2'-bipyridine-5,5'-dicarboxylate;5,5'-diethyl [2,2'-bipyridine]-5,5'-dicarboxylate;5,5'-Bis(ethoxycarbonyl)-2,2'-bipyridine;[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester;ethyl 6-(5-ethoxycarbonylpyridin-2-yl)pyridine-3-carboxylate
• CAS NO: 1762-46-5
• Molecular Formula: C₁₆H₁₆N₂O₄
• Molecular Weight: 300.30924
• Mol File: 1762-46-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 145-147 °C
• Boiling Point: 428.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.99±0.32(Predicted)
• CAS DataBase Reference: diethyl 2,2'-bipyridine-5,5'-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 2,2'-bipyridine-5,5'-dicarboxylate(1762-46-5)
• EPA Substance Registry System: diethyl 2,2'-bipyridine-5,5'-dicarboxylate(1762-46-5)

Safety Data

• Hazardous Substances Data: 1762-46-5(Hazardous Substances Data)

Usage

General Description

Diethyl 2,2'-bipyridine-5,5'-dicarboxylate (also known as bipyridine dicarboxylate, or DEBPDC) is a type of bipyridine compound with carboxylate groups. It is commonly used in scientific research, especially where metal-organic frameworks (MOFs), coordination chemistry, and luminescent materials are concerned. The carboxylic acid groups make it a reliable bridge connector for creating multi-dimensional networks in MOFs. diethyl 2,2'-bipyridine-5,5'-dicarboxylate has the ability to form complexes with transition metals and can be used as a ligand. The use of DEBPDC has been pivotal in the creation of new compounds with unique properties, beneficial in various technological applications.

Upstream product

• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 64-17-5 ethanol 
• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 
• 151917-39-4 ethyl 6-iodonicotinate 
• 108-99-6 3-Methylpyridine 

Downstream Products

• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 135822-72-9 2,2′-bipyridine-5,5′-dicarbaldehyde 
• 1802-29-5 2,2’-bipyridine-5,5’-dicarbonitrile 
• 63361-65-9 5,5’-bis(hydroxymethyl)-2,2’-bipyridine 

Relevant articles and documents

The folding of a metallopeptide

We have applied solid-phase synthesis methods for the construction of tris(bipyridyl) peptidic ligands that coordinate Fe(ii) ions with high affinity and fold into stable mononuclear metallopeptides. The main factors influencing the folding pathway and ch

Dynamic Stereoselection of Peptide Helicates and Their Selective Labeling of DNA Replication Foci in Cells**

Although largely overlooked in peptide engineering, coordination chemistry offers a new set of interactions that opens unexplored design opportunities for developing complex molecular structures. In this context, we report new artificial peptide ligands t

Remote control of bipyridine-metal coordination within a peptide dendrimer

The metal coordinating ability of a bipyridine ligand at the core of a peptide dendrimer was found to be controlled by the nature of amino acids placed at the dendrimer periphery, with coordination being promoted by anionic residues and inhibited by catio

A Molecular Water-Oxidation Catalyst Derived from Ruthenium Diaqua Bis(2,2'-bipyridyl-5,5'-dicarboxylic acid)

Controlled-potential electrolysis of cis-RuIIL2(OH2)22+ (where L is 2,2'-bipyridyl-5,5'-dicarboxylic acid) in 0.5 M H2SO4 solutions leads to the formation of a relatively durable and active molecular water-oxidation catalyst.Detailed analyses by UV-visible absorption spectrophotometry, resonance Raman spectrophotometry, electrochemical measurements, HPLC, and elemental analysis indicate that the water-oxidation catalyst is an oxo-bridged dimer, L2(H2O)Ru-O-Ru(OH2)L2.The synthesis, spectrophotometric, and redox properties of the monomeric and dimeric ruthenium complexes have been characterized.The effectiveness of the oxo-bridged complex as a water-oxidation catalyst has been evaluated by electrochemical and spectrophotometric analyses and by determination of oxygen production.This newly discovered homogeneous catalyst is highly effective in mediating the thermal and visible-light-induced generation of oxygen from water.A comparison is made between the monomer and dimer and various analogues of the complexes.The presence of the COOH groups at the 5,5' positions of the bipyridyl ligands correlates with the unusual and favorable properties of cis-RuL2(OH2)2 and L2(OH2)Ru-O-Ru(OH2)L2.Dimeric ruthenium complexes of similar structure are also formed during the thermolysis and photolysis of Ru(II) tris(2,2'-bipyridyl-5,5'-dicarboxylic acid), RuL32+, in 0.5 M H2SO4 solutions containing peroxodisulfate.

A comparative study of Ru(ii) cyclometallated complexes versus thiocyanated heteroleptic complexes: Thermodynamic force for efficient dye regeneration in dye-sensitized solar cells and how low could it be?

Four novel Ru(ii) bipyridyl complexes MH12-15 were synthesized and characterized for dye-sensitized solar cells (DSSCs). Their photovoltaic performance including incident photon-to-current conversion efficiency (IPCE), total solar-to-power conversion efficiency (η%) and ground and excited state oxidation potentials and photoelectrochemical properties were evaluated on mesoporous nanocrystalline TiO2 and compared with the benchmark N719-dye under the same experimental conditions. MH12-15 showed stronger MLCT with significantly higher molar extinction coefficient for the lower energy absorption bands at 553 nm (27500 M-1 cm-1), 554 nm (34605 M-1 cm-1), 577 nm (23300 M-1 cm-1), and 582 nm (39000 M-1 cm-1), respectively, than that of N719 (14200 M-1 cm-1). The introduction of a cyclometallated ligand in dyes MH14 and 15 improved the optical properties and red-shifts of 24 nm and 28 nm, respectively, compared to the non-cyclometallated analogs MH12 and 13. The red shift in the UV-Vis spectra of MH14 and 15 can be attributed to the destabilization of the HOMO t2g of Ru(ii). However, the destabilization of the HOMO furnished an upward shift of the ground state oxidation potentials (GSOPs) of MH14 and 15 at -5.44 eV and -5.36 eV against vacuum, respectively, which resulted in a driving force of only 0.22 and 0.16 eV for regeneration of dyes MH14 and 15, respectively. In the case of NCS analogs, MH12 and 13, the GSOPs, however, were -5.56 and -5.51 eV, respectively, which produced a driving force of more than 0.25 eV for dye regeneration. The nanosecond transient absorbance measurements showed that the time needed for the oxidized forms of MH12-MH15 to regenerate the neutral dye is 6 μs, 4 μs, 13 μs and 18 μs, respectively, compared to N719 (2.3 μs). These kinetic data confirmed that the weak thermodynamic force, small negative free energy (-ΔG), for regeneration of MH14 and 15 neutral dyes makes the dye regeneration process kinetically sluggish, which contributed significantly to the loss of both photocurrent and photovoltage. This study clearly elucidated that although cyclometallation may produce significantly better light harvesting, the driving force of less than 0.25 eV is not sufficiently enough for effective dye regeneration. the Partner Organisations 2014.

Metallo-Organozymes with Specific Proteolytic Activity

Metallopeptides that show efficiency and selectivity in peptide bond cleavage in water at room temperature and neutral conditions are presented. These small and versatile organozymes take advantage of metal-coordinating building blocks that are strategica

Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts

RhL2 complexes of phosphonate-derivatized 2,2′-bipyridine (bpy) ligands L were immobilized on titanium oxide particles generated in situ. Depending on the structure of the bipy ligand—number of tethers (1 or 2) to which the phosphonate end groups are attached and their location on the 2,2′-bipyridine backbone (4,4′-, 5,5′-, or 6,6′-positions)—the resulting supported catalysts showed comparable chemoselectivity but different kinetics for the hydrogenation of 6-methyl-5-hepten-2-one under hydrogen pressure. Characterization of the six supported catalysts suggested that the intrinsic geometry of each of the phosphonate-derivatized 2,2′-bipyridines leads to supported catalysts with different microstructures and different arrangements of the RhL2 species at the surface of the solid, which thereby affect their reactivity.