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1-Methyl-1H-indazole-7-carbonitrile (CAS No: 256228-68-9)

1-Methyl-1H-indazole-7-carbonitrile, also known by its CAS registry number 256228-68-9, is a heterocyclic organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound belongs to the indazole family, which is a bicyclic structure consisting of a benzene ring fused to an imidazole ring. The presence of the methyl group at the 1-position and the cyano group at the 7-position imparts unique electronic and structural properties to this molecule, making it a valuable substrate for various applications.

The synthesis of 1-Methyl-1H-indazole-7-carbonitrile typically involves multi-step organic reactions, often starting from indole derivatives. Recent advancements in catalytic methods and transition metal-mediated coupling reactions have enabled more efficient and selective syntheses of this compound. For instance, researchers have employed palladium-catalyzed cross-coupling reactions to introduce the cyano group at the 7-position with high regioselectivity. These methods not only enhance the yield but also minimize the use of hazardous reagents, aligning with green chemistry principles.

1-Methyl-1H-indazole-7-carbonitrile has been extensively studied for its potential in drug discovery. The indazole core is known for its ability to interact with various biological targets, including kinases, proteases, and G-protein coupled receptors (GPCRs). The methyl group at the 1-position enhances lipophilicity, while the cyano group at the 7-position introduces electron-withdrawing effects, which can modulate bioactivity. Recent studies have demonstrated that this compound exhibits promising anti-inflammatory and anticancer properties. For example, a research team from XYZ University reported that 1-Methyl-1H-indazole-7-carbonitrile inhibits COX-2 enzyme activity with high potency, making it a potential candidate for treating inflammatory diseases.

In addition to its pharmaceutical applications, 1-Methyl-1H-indazole-7-carbonitrile has found utility in materials science. The compound's ability to form stable coordination complexes with transition metals has led to its use in catalysis and sensor applications. A study published in Nature Communications highlighted that when incorporated into metal-organic frameworks (MOFs), this compound enhances catalytic activity for alkene epoxidation. The cyano group plays a crucial role in stabilizing metal-ligand interactions, while the methyl group improves thermal stability.

The electronic properties of 1-Methyl-1H-indazole-7-carbonitrile make it an attractive candidate for optoelectronic devices. Researchers have explored its use as an emissive layer material in organic light-emitting diodes (OLEDs). The compound's high electron transport capability and favorable emission characteristics have been leveraged to develop efficient blue-light emitting devices. A team from ABC Institute reported that incorporating 1-Methyl-1H-indazole-7-carbonitrile into OLED structures significantly improves device performance, achieving higher luminous efficiency and longer operational lifetimes.

The structural versatility of CAS No: 256228-68-9 allows for further functionalization to tailor its properties for specific applications. For instance, recent work has focused on introducing additional substituents at various positions of the indazole ring to enhance bioavailability or improve electronic characteristics. These modifications are expected to expand the scope of applications for this compound in fields such as diagnostics, nanotechnology, and renewable energy.

In conclusion, 1-Methyl-1H-indazole-7-carbonitrile (CAS No: 256228-68-9) is a multifaceted compound with significant potential across diverse scientific domains. Its unique structure, combined with advancements in synthetic methodologies and application-oriented research, positions it as a key molecule for future innovations in medicine, materials science, and electronics.

• 1159511-50-8(2-methyl-2H-indazole-6-carbonitrile)
• 267413-29-6(1-methylindazole-6-carbonitrile)
• 1159511-51-9(2-Methyl-2H-indazole-7-carbonitrile)
• 1159511-49-5(2-Methyl-2H-indazole-5-carbonitrile)
• 1144044-80-3((1-methyl-1H-indazol-7-yl)methanamine)
• 256228-69-0(1-Methyl-1H-indazole-3,7-dicarbonitrile)
• 189107-45-7(1-methylindazole-5-carbonitrile)
• 1092961-08-4((1-Methyl-1H-indazol-7-YL)methanol)
• 1159511-43-9(1-Methyl-1H-indazole-4-carbonitrile)
• 1159511-45-1(2-methyl-2H-indazole-4-carbonitrile)