24573-15-7

Basic information

• Product Name: 4,4'-BIPYRIDINE 1,1'-DIOXIDE
• Synonyms: 4,4'-BIPYRIDINE 1,1'-DIOXIDE;4-(4-PYRIDIN-N-OXIDE)PYRIDINE-N-OXIDE;4,4''-DIPYRIDYL N,N''-DIOXIDE;4,4'-Bipyridine N,N'-dioxide;4-(1-oxidopyridin-4-ylidene)pyridin-1-ium 1-oxide
• CAS NO: 24573-15-7
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• Mol File: 24573-15-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 298-299 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• PKA: 0.03±0.10(Predicted)
• CAS DataBase Reference: 4,4'-BIPYRIDINE 1,1'-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-BIPYRIDINE 1,1'-DIOXIDE(24573-15-7)
• EPA Substance Registry System: 4,4'-BIPYRIDINE 1,1'-DIOXIDE(24573-15-7)

Safety Data

• Hazardous Substances Data: 24573-15-7(Hazardous Substances Data)

Usage

General Description

4,4'-Bipyridine 1,1'-dioxide, also known as Bipyridine N-oxide, is a chemical compound with the molecular formula C10H8N2O2. It is a bidentate ligand, meaning it can form coordination complexes with transition metals, and is commonly used in metal-catalyzed reactions for its ability to stabilize metal atoms and facilitate electron transfer. Bipyridine N-oxide has also been studied for its potential pharmaceutical and medicinal applications, particularly in the field of cancer research and therapeutics, due to its ability to interact with DNA and potentially inhibit tumor cell growth. Additionally, it is used in organic synthesis as a reagent for the oxidation of alcohols and amination reactions. Bipyridine N-oxide is typically produced through the oxidation of 4,4'-bipyridine with peracids or hydrogen peroxide, and it is a light yellow crystalline solid at room temperature.

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

Upstream product

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

Downstream Products

• 553-26-4 4,4'-bipyridine 
• 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) 
• 1311266-41-7 poly[aqua(μ2-benzene-1,4-dicarboxylato)(μ2-4,4'-bipyridine N,N'-dioxide)cadmium(II)] 

Relevant articles and documents

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.

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.