124558-62-9

Basic information

• Product Name: 2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE
• Synonyms: TETRAMETHYL 4,4'-BIPYRIDINE-2,2',6,6'-TETRACARBOXYLATE;2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE
• CAS NO: 124558-62-9
• Molecular Formula: C18H16N2O8
• Molecular Weight: 388.33
• Mol File: 124558-62-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 577.9°Cat760mmHg
• Flash Point: 303.3°C
• Appearance: /
• Density: 1.326g/cm³
• CAS DataBase Reference: 2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE(124558-62-9)
• EPA Substance Registry System: 2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE(124558-62-9)

Safety Data

• Hazardous Substances Data: 124558-62-9(Hazardous Substances Data)

Usage

General Description

2,2',6,6'-Tetrakis(methoxycarbonyl)-4,4'-bipyridine, also known as TMCBP, is a chemical compound with a molecular formula C28H24N2O8. It is a highly symmetrical, tetra-substituted bipyridine derivative that is widely used in coordination chemistry and material science. TMCBP has a unique structure with four methoxycarbonyl groups attached to the four nitrogen atoms of the bipyridine core, which makes it a versatile ligand for various metal ions. It is often employed in the design of metal-organic frameworks (MOFs) and coordination polymers due to its ability to form strong coordination bonds with metal ions. In addition, TMCBP has been studied for its potential applications in catalysis, sensors, and optoelectronic devices due to its interesting photophysical and electrochemical properties.

Upstream product

• 67-56-1 methanol 
• 124558-60-7 [4,4'-bipyridine]-2,2',6,6'-tetracarboxylic acid 
• 108-48-5 2,6-dimethylpyridine 
• 6662-72-2 2,2’,6,6’-tetramethyl-4,4’-bipyridine 
• 499-51-4 Chelidamic acid 
• 5371-70-0 dimethyl 4-chloro-2,6-pyridinedicarboxylate 

Relevant articles and documents

A Highly Stable Organic Radical Cation

Functionalization of a methylviologen with four methyl ester substituents significantly facilitates the first two reduction steps. The easily generated radical cation shows markedly improved air stability compared to the parent methylviologen, making this derivative of interest in organic electronic applications.

A Convenient Synthesis of 2,2',6,6'-Tetramethyl-4,4'-bipyridine and Its Oxidation to 2,2',6,6'-Tetracarboxy-4,4'-bipyridine

By reaction of 2,6-dimethylpyridine (1b) with sodium the tetrahydro-4,4'-bipyridine bis-sodium salt 2b is formed.Of different dehydrogenation reagents tested, only sulfur dioxide affords the title compound 3b, in 49percent overall yield.By oxidation of 3b with chromium trioxide, 2,2',6,6'-tetracarboxy-4,4'-bipyridine (3c, 70percent) is produced, a valuable precursor for several 2,2',6,6'-tetrasubstituted 4,4'-bipyridines, e.g., the corresponding acid chloride 3d and the carboxylic esters 3e and 3f.