4,5-Imidazoledicarboxylic acid
[CAS# 570-22-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 4,5-Imidazoledicarboxylic acid
• Synonyms: Imidazole-4,5-dicarboxylic acid
• Molecular Formula: C₅H₄N₂O₄
• Molecular Weight: 156.10
• CAS Registry Number: 570-22-9
• EC Number: 209-327-5
• SMILES: C1=NC(=C(N1)C(=O)O)C(=O)O

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*, 1.749 g/mL (Expl.)
• Melting point: 280-285 °C (dec.) (Expl.)
• Index of Refraction: 1.683, Calc.^*
• Boiling Point: 631.1±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 335.5±27.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

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

Discovery and Applications

4,5-Imidazoledicarboxylic acid is an organic compound containing an imidazole ring with two carboxyl groups attached at positions 4 and 5. The molecular formula of 4,5-imidazoledicarboxylic acid is C5H4N2O4, and it is a heterocyclic compound that belongs to the imidazole family. Imidazole derivatives, including 4,5-imidazoledicarboxylic acid, are of significant interest in various areas of chemistry, biochemistry, and material science due to their versatile chemical reactivity and potential biological activity.

The discovery of 4,5-imidazoledicarboxylic acid can be traced to the early work on imidazole derivatives. Imidazole itself was first synthesized in the 19th century, and since then, numerous substituted imidazoles have been studied for their properties and applications. The introduction of carboxyl groups at the 4 and 5 positions of the imidazole ring imparts specific functional properties that make 4,5-imidazoledicarboxylic acid valuable in various fields, particularly in the synthesis of bioactive compounds and materials.

One of the key applications of 4,5-imidazoledicarboxylic acid is in the field of medicinal chemistry. Imidazole derivatives are known for their biological activities, and the addition of carboxyl groups at specific positions can influence their interaction with biological targets. Compounds containing the imidazole ring system, such as 4,5-imidazoledicarboxylic acid, have been studied for their ability to act as inhibitors of enzymes and receptors involved in various diseases, including cancer and inflammation. Research has shown that imidazole derivatives can serve as scaffold structures for the design of novel therapeutic agents targeting specific pathways in disease mechanisms.

4,5-Imidazoledicarboxylic acid also plays a role in the synthesis of coordination compounds. The presence of the carboxyl groups makes the compound a potential ligand in coordination chemistry, where it can bind to metal ions to form stable complexes. These metal-ligand interactions are important in catalysis and material science, where imidazole-based ligands are often used in the design of catalysts for organic reactions or in the preparation of functional materials such as sensors or molecular electronics.

In the field of materials science, 4,5-imidazoledicarboxylic acid has been explored for its potential as a building block in the creation of metal-organic frameworks (MOFs). MOFs are porous materials made up of metal ions or clusters coordinated to organic ligands, and they are used in a wide range of applications, including gas storage, catalysis, and drug delivery. The ability of 4,5-imidazoledicarboxylic acid to chelate metal ions and form stable frameworks makes it a promising candidate in the development of new MOF materials with tailored properties.

References

2023. Structure and Acid-Base Properties of 1-Propylimidazole-4,5-dicarboxylic Acid. Russian Journal of General Chemistry, 93(5).
DOI: 10.1134/s1070363223050079

2019. Synthesis of substituted imidazole-4,5-dicarboxylic acids. Russian Chemical Bulletin, 68(4).
DOI: 10.1007/s11172-019-2474-7

2021. Opportunities and Challenges in Biomedical Applications of Metal-Organic Frameworks. Journal of Inorganic and Organometallic Polymers and Materials, 31(11).
DOI: 10.1007/s10904-021-02118-7