24573-15-7

Usage

Uses

Used in Chemical Catalysis:
4,4'-Bipyridine 1,1'-dioxide is used as a bidentate ligand in chemical catalysis for its ability to stabilize transition metal atoms and facilitate electron transfer, which is crucial in various metal-catalyzed reactions.
Used in Pharmaceutical and Medicinal Research:
In the Pharmaceutical Industry, 4,4'-Bipyridine 1,1'-dioxide is used as a potential therapeutic agent for its capacity to interact with DNA and its potential to inhibit tumor cell growth, making it a candidate for cancer research and treatment.
Used in Organic Synthesis:
4,4'-Bipyridine 1,1'-dioxide is utilized as a reagent in organic synthesis for the oxidation of alcohols and amination reactions, contributing to the formation of desired organic compounds in chemical processes.

InChI:InChI=1/C10H8N2O2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H

Upstream product

• 553-26-4 4,4'-bipyridine 
• 1121-76-2 4-chloropyridine N-oxide 

Downstream Products

• 53829-09-7 4,4'-bis(3,3'-dicyano)pyridine 
• 1144113-64-3 p-phenylenediboronic acid*(4,4'-bipyridine N,N'-dioxide) 
• 1239195-03-9 Cu₂(benzoate)4(4,4'-bipyridyl-N,N'-dioxide) 
• 1279114-01-0 C₆H₆ClNO₂S*C₁₀H₈N₂O₂ 

Relevant academic research and scientific papers

Syntheses of bipyridine-N-oxides and bipyridine-N,N'-dioxides

Dimethyldioxirane (DMD) was used to synthesize heterocyclic aromatic N-oxides enabling the product isolation and reaction solutions to be free of potentially dangerous peroxide intermediates. Additionally, this work combines important crystallographic, spectroscopic, and melting point data to shed light on inconsistent literature previously reported for the identity of 2,4'-bipyridine-N'-oxide.

4,4′-bipyridine-N-monoxide. A hybrid ligand for building networks using a combination of metal-ligand and hydrogen-bonding interactions

The ligand 4,4′-bipyridine-N-monoxide, (BIPYMO) coordinates through the pyridine N-donor to Pt(ii) and Pd(ii) to form square planar [ML 4]2+ complexes and to Cu(ii) and Zn(ii) to form octahedral trans-[M(H2O)2L4]2+ complexes. Single crystal X-ray structures show that these individual building blocks are organized via hydrogen bonding through the external N-oxide O-atoms to form 2D and 3D networks. The Royal Society of Chemistry.

Novel chiral oxazoline ligands for potential charge-transfer effects in the Rh(I)-catalysed enantioselective hydrosilylation

Novel 2-(4,4′-bipyridin-2-yl)oxazolines, bearing a chiral oxazoline moiety, were synthesised starting from 4,4′-bipyridine and selectively monomethylated in the N′-position. After coordination to rhodium these electron-poor ligands are supposed to exhibit charge-transfer effects with electron-donating substrates in the Rh(I)-catalysed enantioselective hydrosilylation (see next publication). Similar effects were expected from 4,4′-bipyridine- and pyrazine-bisoxazolines after complexation with rhodium. For comparison 2-(4-phenylpyridin-2-yl)oxazoline ligands were synthesised. Rh(I)-complexes of selected ligands were prepared and characterised, including an X-ray structure analysis.