Chemical Identity and Structural Features

6-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid belongs to the imidazo[1,2-a]pyridine class of fused bicyclic heteroaromatics, a scaffold of significant interest in contemporary drug discovery. The compound consists of an imidazole ring fused to a pyridine ring via the 1,2-a fusion pattern, yielding a planar, electron-rich aromatic system with two nitrogen atoms contributing to its unique electronic profile.

Two key functional handles distinguish this compound: (1) an aryl bromide at the 6-position, which serves as an excellent substrate for metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings; and (2) a carboxylic acid at the 8-position, enabling amide bond formation, esterification, and further diversification through standard synthetic transformations. This dual functionality makes the molecule a highly versatile bifunctional building block.

The molecular formula is C₈H₅BrN₂O₂, with a calculated molecular weight of approximately 241.04 g/mol. Researchers should verify the exact CAS number, purity, and physical constants (melting point, solubility) against the certificate of analysis (CoA) supplied with each lot from Aladdin Scientific (SKU: B178112).

Applications in Synthesis and Drug Discovery

The imidazo[1,2-a]pyridine core is a privileged scaffold appearing in numerous bioactive compounds and approved pharmaceuticals, including agents with kinase-inhibitory, antimicrobial, and central nervous system activity. Introduction of substituents at the 6- and 8-positions allows fine-tuning of pharmacokinetic and pharmacodynamic properties.

Cross-coupling chemistry: The 6-bromo substituent enables efficient palladium- or nickel-catalyzed cross-coupling reactions. Suzuki–Miyaura coupling with arylboronic acids, Sonogashira coupling with terminal alkynes, and Buchwald–Hartwig amination are all accessible, allowing rapid construction of diverse analogues for structure–activity relationship (SAR) studies.

Amide and ester formation: The 8-carboxylic acid participates readily in peptide-coupling protocols using standard reagents (e.g., HATU, EDC/HOBt, DCC) or can be converted to an acid chloride for further reactivity. Methyl or ethyl esters can also be prepared under Fischer or Mitsunobu conditions to serve as masked carboxylic acid equivalents.

Library synthesis: The bifunctionality of 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid supports parallel synthesis workflows. Sequential functionalization — first amide bond formation at the carboxylic acid, then cross-coupling at the bromide — enables efficient generation of focused libraries for high-throughput screening.

Handling, Safety, and Storage Guidelines

Personal protective equipment (PPE): When handling 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid, wear appropriate PPE including nitrile gloves, safety glasses or goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimise inhalation exposure to fine particulates.

Storage: Store the compound in a tightly sealed container in a cool, dry, and dark environment. Protect from moisture and prolonged exposure to light to prevent potential degradation. The recommended storage temperature and any specific incompatibilities should be confirmed in the Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU B178112.

Stability: As a solid heteroaromatic carboxylic acid, this compound is expected to be stable under recommended storage conditions. However, prolonged exposure to moisture may affect purity. Always allow the container to equilibrate to room temperature before opening to avoid condensation onto the solid.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations for halogenated organic compounds. Consult the SDS for specific disposal guidance.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid under SKU B178112. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity (typically assessed by HPLC or NMR), appearance, and lot-specific analytical data. Researchers are advised to request and review the CoA before use in critical synthetic steps.

Purity considerations: For medicinal chemistry and SAR work, high-purity material (≥95% or better) is strongly recommended to ensure reproducibility of biological and chemical results. If higher purity grades are required, contact Aladdin Scientific customer support to discuss available options.

Ordering: The compound can be ordered directly through the Aladdin Scientific website. For bulk quantities or custom packaging, researchers and procurement teams should contact Aladdin Scientific directly for pricing and availability. Standard terms regarding shipping, payment, and returns apply as outlined in Aladdin Scientific's procurement policies.