2,2'-Bipyridine-4,4'-dicarboxylic acid
[CAS# 6813-38-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2,2'-Bipyridine-4,4'-dicarboxylic acid
• Synonyms: 4,4'-Dicarboxy-2,2'-bipyridine
• Molecular Formula: C₁₂H₈N₂O₄
• Molecular Weight: 244.21
• CAS Registry Number: 6813-38-3
• EC Number: 626-224-4
• SMILES: C1=CN=C(C=C1C(=O)O)C2=NC=CC(=C2)C(=O)O

Properties

• Water solubility: insoluble
• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.654, Calc.^*
• Boiling Point: 677.0±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 363.2±31.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2,2'-Bipyridine-4,4'-dicarboxylic acid is an important organic compound that belongs to the class of bipyridine derivatives, which are widely recognized for their versatility in coordination chemistry and applications in various fields. This compound features a bipyridine core, where two pyridine rings are connected by a carbon-carbon bond at the 2 and 2' positions, with carboxylic acid groups (-COOH) attached at the 4 and 4' positions. The presence of these functional groups enhances the reactivity of the compound, making it valuable for a range of chemical reactions and industrial applications.

The discovery of bipyridine derivatives dates back to the late 19th century, with the synthesis of various bipyridine compounds being explored due to their ability to form coordination complexes with metal ions. Among these, 2,2'-bipyridine itself has played a pivotal role in the development of coordination chemistry and catalysis. The addition of carboxylic acid groups at specific positions, such as in 2,2'-bipyridine-4,4'-dicarboxylic acid, has expanded the scope of this compound's application, particularly in fields where metal-ligand interactions are of interest.

One of the primary applications of 2,2'-bipyridine-4,4'-dicarboxylic acid lies in the field of metal coordination chemistry. This compound is used as a ligand in the formation of metal complexes, where the carboxylate groups coordinate with metal ions such as copper, zinc, and palladium. These complexes have proven valuable in a range of catalytic processes, including organic synthesis and polymerization reactions. The ability of 2,2'-bipyridine-4,4'-dicarboxylic acid to form stable complexes with transition metals makes it an essential building block for the development of homogeneous catalysts in various chemical transformations.

In addition to its role in catalysis, 2,2'-bipyridine-4,4'-dicarboxylic acid has significant applications in materials science, particularly in the development of functional materials. The compound is used in the synthesis of metal-organic frameworks (MOFs), which are a class of porous materials formed by metal ions coordinated to organic ligands. MOFs based on 2,2'-bipyridine-4,4'-dicarboxylic acid exhibit high surface areas, tunable porosity, and chemical stability, making them useful in a variety of applications such as gas storage, separation processes, and sensing.

In the field of electrochemistry, 2,2'-bipyridine-4,4'-dicarboxylic acid is utilized in the design of electroactive materials. Metal complexes formed from this ligand can be incorporated into electrodes for batteries, fuel cells, and supercapacitors, where their ability to facilitate electron transfer is crucial. The carboxylate groups in the ligand help stabilize the metal center and enhance the conductivity of the resulting material, making it suitable for energy storage and conversion devices.

Furthermore, this compound has found applications in the development of chelating agents for medical imaging and therapy. The metal complexes of 2,2'-bipyridine-4,4'-dicarboxylic acid are being explored for use in contrast agents for magnetic resonance imaging (MRI) and as radiopharmaceuticals in cancer treatment. The carboxylate groups allow for efficient binding of metal ions, which can be utilized in targeting specific tissues and enhancing the effectiveness of diagnostic and therapeutic procedures.

In summary, 2,2'-bipyridine-4,4'-dicarboxylic acid is a versatile compound with a broad range of applications in chemistry, materials science, and medicine. Its role as a ligand in metal coordination chemistry, its use in the synthesis of functional materials, and its potential in electrochemical and medical applications make it an invaluable substance in modern scientific research and industry.