Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate)

Base Information

• Chemical Name: Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate)
• CAS No.: 174397-53-6
• Molecular Formula: C18H26N2O6P2
• Molecular Weight: 428.362
• Hs Code.: 2933399090
• European Community (EC) Number: 808-578-3
• DSSTox Substance ID: DTXSID60431735
• Nikkaji Number: J943.702I
• Mol file: 174397-53-6.mol

Synonyms:174397-53-6;Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate);TETRAETHYL 2,2'-BIPYRIDINE-4,4'-BISPHOSPHONATE;4-diethoxyphosphoryl-2-(4-diethoxyphosphorylpyridin-2-yl)pyridine;DTXSID60431735;AG-E-23990;CS-W004605;AS-69748;A921363;4,4'-DIETHYL ESTER PHOSPHONATE-2,2'-BIPYRIDINE;Tetraethyl[2,2'-bipyridine]-4,4'-diylbis(phosphonate);2,2'-Bipyridine-4,4'-diylbis(phosphonic acid diethyl) ester;diethyl [4'-(diethoxyphosphoryl)-[2,2'-bipyridin]-4-yl]phosphonate;P,P'-[[2,2'-bipyridine]-4,4'-diyl]bisphosphonic acid, 97% (HPLC)

Chemical Property of Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate)

Chemical Property:

• Boiling Point: 553.43oC at 760 mmHg
• Flash Point: 288.504oC
• PSA: 116.46000
• Density: 1.255g/cm3
• LogP: 3.92640
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 428.12661055
• Heavy Atom Count: 28
• Complexity: 496

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetraethyl2,2''-Bipyridine-4,4''-bisphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1=CC(=NC=C1)C2=NC=CC(=C2)P(=O)(OCC)OCC)OCC
• Use Description: Tetraethyl 2,2'-bipyridine-4,4'-bisphosphonate, a compound with a unique chemical structure, serves various roles across different fields. In the realm of coordination chemistry and catalysis, it is employed as a ligand to coordinate with metal ions, facilitating complex formation and catalytic reactions. This compound is crucial in the development of new catalytic processes with applications in organic synthesis and material science. In the field of materials science, it plays a significant role as a precursor in the synthesis of metal-organic frameworks (MOFs) and other advanced materials, contributing to the design of innovative materials with diverse properties and applications, such as gas storage, sensing, and catalysis. Additionally, in academic research, Tetraethyl 2,2'-bipyridine-4,4'-bisphosphonate serves as a valuable tool for investigating the coordination chemistry of metal ions and ligands, leading to a deeper understanding of chemical interactions. Its multifaceted utility underscores its importance in advancing chemistry, materials science, and scientific exploration, where it plays a pivotal role in the development of novel materials and catalytic processes.

Technology Process of Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate)

There total 2 articles about Tetraethyl [2,2'-bipyridine]-4,4'-diylbis(phosphonate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.6%

4,4'-dibromo-2,2'-bipyridine (18511-71-2) + phosphonic acid diethyl ester (762-04-9) → tetraethyl 2,2′-bipyridine-4,4′-diyldiphosphonate (174397-53-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; triphenylphosphine; In toluene; at 110 ℃; for 6h;

DOI:10.1016/S0040-4039(98)00647-9

Reference yield:

4,4'-Dimethoxy-2,2'-bipyridin (17217-57-1) → tetraethyl 2,2′-bipyridine-4,4′-diyldiphosphonate (174397-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus(V) oxybromide / N,N-dimethyl-formamide / 19 h / 0 - 105 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / toluene / 4 h / 110 °C / Inert atmosphere; Schlenk technique

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; phosphorus(V) oxybromide; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ic4014976

Reference yield: 100.0%

tetraethyl 2,2′-bipyridine-4,4′-diyldiphosphonate (174397-53-6) → 4,4′-bis(phosphonic acid)-2,2′-bipyridine (194800-56-1)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.dyepig.2013.12.018

upstream raw materials:

4,4'-dibromo-2,2'-bipyridine

phosphonic acid diethyl ester

4,4'-Dimethoxy-2,2'-bipyridin

Downstream raw materials:

4,4′-bis(phosphonic acid)-2,2′-bipyridine

Refernces

• 1、 Amthor, Sebastian,Keil, Philip,Nauroozi, Djawed,Perleth, Daniel,Rau, Sven. "A Phosphonate Substituent in a 1,10-Phenanthroline Ligand Boosts Light-Driven Catalytic Water Oxidation Performance Sensitized by Ruthenium Chromophores". . p. 4790 - 4798. Retrieved 2021/11/30.
• 2、 Neuthe, Katja,Bittner, Florian,Stiemke, Frank,Ziem, Benjamin,Du, Juan,Zellner, Monika,Wark, Michael,Schubert, Thomas,Haag, Rainer. "Phosphonic acid anchored ruthenium complexes for ZnO-based dye-sensitized solar cells". . p. 24 - 33. Retrieved 2014/02/14.