Product Description
3-Fluoro-5-iodopyridine、757950-13-3
AI Product Description
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3-Fluoro-5-iodopyridine is a specialized heterocyclic building block widely utilized in modern organic synthesis and medicinal chemistry. With the molecular formula C₅H₂FI N and a CAS registry number of 149206-87-7, this compound serves as a critical intermediate for the development of complex pharmaceutical agents, agrochemicals, and advanced functional materials. The molecule features a pyridine ring substituted with a fluorine atom at the 3-position and an iodine atom at the 5-position, creating a unique electronic landscape that facilitates diverse cross-coupling reactions.
The primary application of 3-fluoro-5-iodopyridine lies in its role as a substrate for palladium-catalyzed cross-coupling methodologies, such as Suzuki-Miyaura, Stille, and Sonogashira couplings. The carbon-iodine bond offers high reactivity, allowing chemists to efficiently introduce various aryl or vinyl groups into the pyridine scaffold. Simultaneously, the presence of the fluorine atom enhances the metabolic stability of final drug candidates and can modulate lipophilicity and binding affinity within biological targets. This dual functionality makes it indispensable for constructing kinase inhibitors, GPCR ligands, and other bioactive molecules containing substituted pyridine cores.
In material science, derivatives synthesized from this precursor are explored for use in organic light-emitting diodes (OLEDs) and photovoltaic materials due to their tunable electronic properties. The specific substitution pattern allows for precise control over the energy levels of frontier orbitals, optimizing device performance. Furthermore, the compound is valued in academic research for mechanistic studies regarding halogen bonding and reaction kinetics. Its commercial availability supports rapid prototyping in drug discovery pipelines, enabling researchers to access novel chemical space efficiently. Safety protocols during handling are essential, as with most organohalides, requiring appropriate personal protective equipment and ventilation to mitigate potential health risks associated with exposure. Overall, 3-fluoro-5-iodopyridine stands as a versatile tool bridging fundamental organic chemistry and applied industrial innovation.