ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives 2,2'-Bipyridine-5,5'-dicarboxylic acid

2,2'-Bipyridine-5,5'-dicarboxylic acid

Product Name2,2'-Bipyridine-5,5'-dicarboxylic acid
CAS1802-30-8
MFC12H8N2O4
MW244.2
EINECS626-338-4
MOL File1802-30-8.mol

Chemical Properties

Melting point	>360 °C(lit.)
Boiling point	521.0±50.0 °C(Predicted)
Density	1.469±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO (Very Slightly, Heated)
form	Solid
pka	1.95±0.10(Predicted)
color	Off-White
InChI	InChI=1S/C12H8N2O4/c15-11(16)7-1-3-9(13-5-7)10-4-2-8(6-14-10)12(17)18/h1-6H,(H,15,16)(H,17,18)
InChIKey	KVQMUHHSWICEIH-UHFFFAOYSA-N
SMILES	C1(C2=NC=C(C(O)=O)C=C2)=NC=C(C(O)=O)C=C1
CAS DataBase Reference	1802-30-8(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Description

2,2''-Bipyridine-5,5''-dicarboxylic acid is a heterocyclic building block. It has been used in the synthesis of metal-organic frameworks for water oxidation, organic photocatalysis, and carbon dioxide reduction.

Chemical Properties

White powder

Uses

A Nicotinic acid (N429250) derivative for treatment of hypercholesterolemia and hyperlipidemia and cardiovascular disease.

Synthesis

1762-34-1

1802-30-8

The general procedure for the synthesis of 2,2'-bipyridine-5,5'-dicarboxylic acid from 5,5'-dimethyl-2,2'-bipyridine was carried out as follows: 5,5'-dimethyl-2,2'-bipyridine (1.0 g) was dissolved in water (35 ml) and potassium permanganate (KMnO4, 6.0 g) was added. The reaction mixture was refluxed overnight under magnetic stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming that the feedstock was completely consumed, the reaction mixture was filtered to remove the generated manganese dioxide (MnO2). The filtrate was concentrated to about 5 mL. Subsequently, the concentrate was acidified with 35% aqueous hydrochloric acid and the mixture was placed in a refrigerator overnight. The precipitated white precipitate was collected by filtration and washed several times with water to give 2,2'-bipyridine-5,5'-dicarboxylic acid (1.0 g, 74% yield) as a final white powder.

References

[1] Dalton Transactions, 2008, # 15, p. 2054 - 2060
[2] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[3] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[4] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
[5] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885

2,2'-Bipyridine-5,5'-dicarboxylic acid

Chemical Properties

Safety Information

Usage And Synthesis

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