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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

Comprehensive Overview of 3-Bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (CAS No. 1190321-08-4)

3-Bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (CAS No. 1190321-08-4) is a heterocyclic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural properties. This compound belongs to the pyrrolopyridine family, a class of nitrogen-containing heterocycles known for their versatile applications in drug discovery and material science. Researchers are increasingly exploring its potential as a building block for kinase inhibitors and other bioactive molecules, aligning with the growing demand for small-molecule therapeutics in oncology and neurology.

The molecular structure of 3-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine features both bromine and chlorine substituents, which enhance its reactivity in cross-coupling reactions like Suzuki-Miyaura and Buchwald-Hartwig couplings. These transformations are critical for constructing complex architectures in medicinal chemistry, making this compound a valuable intermediate. Recent studies highlight its utility in developing JAK-STAT inhibitors, a hot topic in autoimmune disease research, as evidenced by rising searches for "JAK inhibitor synthesis" and "pyrrolopyridine derivatives" in scientific databases.

From a synthetic perspective, CAS 1190321-08-4 offers advantages in parallel synthesis and combinatorial chemistry, addressing the pharmaceutical industry's need for high-throughput screening libraries. Its halogenated nature allows for selective functionalization, a feature frequently queried in forums discussing "site-selective heterocycle modification." Moreover, its stability under standard storage conditions (typically 2-8°C under inert atmosphere) makes it practical for industrial-scale applications.

Environmental and regulatory considerations surrounding halogenated compounds have also spurred interest in greener alternatives. While 3-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine itself isn't classified as hazardous under current guidelines, researchers are investigating catalytic bromination methods to reduce waste—a trend reflected in the surge of "sustainable heterocycle synthesis" publications. This aligns with the broader push toward green chemistry in API manufacturing.

Analytical characterization of this compound typically involves HPLC purity analysis (>95% by area normalization) and structural confirmation via 1H/13C NMR and HRMS. These protocols are frequently searched alongside terms like "pyrrolopyridine characterization" and "heterocyclic QC methods." The compound's UV absorption maxima around 270-290 nm also make it suitable for photophysical studies, an area gaining traction in organic electronics research.

In the context of intellectual property, 1190321-08-4 appears in several patents related to kinase modulator development, particularly for inflammatory disorders. This correlates with increasing searches for "pyrrolopyridine patents" and "kinase inhibitor scaffolds." Its cost-effectiveness compared to similar bicyclic heterocycles further enhances its commercial viability for contract research organizations.

Future directions for this compound may include exploration in PROTAC (Proteolysis Targeting Chimeras) technology, where its dual halogenation could enable bifunctional linker attachment—a cutting-edge area with rising Google Scholar citations. As the demand for targeted protein degradation compounds grows, 3-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine is poised to remain relevant in next-generation therapeutic development.

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