5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine(CAS: 754214-56-7)

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is a crystalline solid with a molecular weight of approximately 356.41 g/mol. It has limited solubility in common organic solvents like DMSO and DMF. This compound shows moderate reactivity in boronate coupling reactions and is commonly used as a boronate ligand. It is stable under normal storage conditions but should be stored away from oxidizing agents.

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is synthesized through a one-pot reaction involving the condensation of 4,4,5,5-tetramethyl-2-bora-1,3-dioxaborolan-2-yl isocyanide with 1H-pyrrolo[2,3-b]pyridine. The reaction is typically carried out in the presence of a catalyst such as a palladium complex to achieve high yield and selectivity. The product is isolated by column chromatography or recrystallization.

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is primarily used in the pharmaceutical and materials science industries. It serves as a boronate ligand in cross-coupling reactions, which are crucial for the synthesis of complex organic molecules. Additionally, it finds applications in the development of sensors and semiconductors due to its unique electronic properties.

When handling 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine, it is essential to wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. Work should be conducted in a well-ventilated fume hood to minimize exposure to airborne particles. In case of a spill, immediately neutralize with a suitable reagent and dispose of according to local regulations. Always refer to the Safety Data Sheet (SDS) for specific handling and disposal instructions.