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

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

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(1802-30-8)Related Product Information

• 2,5-Dimethylpyridine
• EPA
• 2,6-Lutidine
• Quinolinic acid
• OXALIC ACID
• DIPIPERIDINOMETHANE
• 4,4'-Bipyridine
• Chromium picolinate
• Folic acid
• Nicotinic acid
• Pyridine-2,6-dicarboxylic acid
• 2,2'-Bipyridine
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Methyl nicotinate
• 6-Methylpyridine-3-carboxylic acid
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 3-Nitropyridine
• NICOTINIC-D4 ACID