Imidazo[1,2-a]pyridine-3-acetic acid ethyl ester
[CAS# 101820-69-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Imidazo[1,2-a]pyridine-3-acetic acid ethyl ester
• Synonyms: ethyl 2-imidazo[1,2-a]pyridin-3-ylacetate
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• CAS Registry Number: 101820-69-3
• SMILES: CCOC(=O)CC1=CN=C2N1C=CC=C2

Properties

• Solubility: Very slightly soluble (0.96 g/L) (25 °C), Calc.^*
• Density: 1.19±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.583, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

Imidazo[1,2-a]pyridine-3-acetic acid ethyl ester is a heterocyclic compound valued in medicinal chemistry and organic synthesis. The molecule features an imidazo[1,2-a]pyridine core, a structure that imparts bioactivity, and an ethyl ester group, which enhances its chemical versatility. This compound has been recognized for its applications in drug discovery, particularly as a scaffold for the development of pharmaceuticals targeting diverse therapeutic areas.

The compound is synthesized through various methods, often beginning with the functionalization of an imidazo[1,2-a]pyridine precursor. A common route involves coupling reactions to introduce the acetic acid moiety, followed by esterification to form the ethyl ester. The inherent reactivity of the imidazo[1,2-a]pyridine system facilitates further derivatization, making it a desirable intermediate for creating structurally complex molecules.

Imidazo[1,2-a]pyridine derivatives, including this compound, have demonstrated significant biological activities. They are particularly noted for their roles as ligands in kinase inhibitors, anti-inflammatory agents, and central nervous system (CNS) modulators. Imidazo[1,2-a]pyridine-3-acetic acid ethyl ester has been explored for its potential in these domains, serving as a starting point for optimizing bioactive molecules with improved pharmacokinetics and efficacy.

Beyond pharmaceuticals, the compound is employed in material science and chemical research. The imidazo[1,2-a]pyridine ring system's electronic properties are harnessed in the design of organic semiconductors and fluorescent probes. Additionally, the ester group allows modifications for the synthesis of functionalized derivatives suited to specific applications.

Research into imidazo[1,2-a]pyridine-3-acetic acid ethyl ester continues to uncover its potential. Advances in synthetic methodologies aim to make its production more efficient and sustainable. Moreover, its role as a versatile intermediate ensures its continued relevance in the development of new materials and therapeutic agents.

References

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