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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Bi- and oligothiophenes Bi- and oligothiophenes
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Bi- and oligothiophenes

Introduction to 5-Bromo-2,2'-bithiophene-5'-carbonitrile (CAS No. 176787-96-5)

5-Bromo-2,2'-bithiophene-5'-carbonitrile, identified by the Chemical Abstracts Service Number (CAS No.) 176787-96-5, is a significant compound in the field of organic synthesis and materials science. This bithiophene derivative features a bromine substituent at the 5-position and a nitrile group at the 5'-position of the two thiophene rings. Its unique structure makes it a valuable intermediate in the synthesis of advanced materials, particularly in organic electronics and pharmaceutical applications.

The compound belongs to the class of bithiophene-based molecules, which are widely studied due to their excellent electronic properties and thermal stability. The presence of both bromine and nitrile functional groups enhances its reactivity, making it a versatile building block for further chemical modifications. In recent years, researchers have been exploring its potential in various applications, including organic light-emitting diodes (OLEDs), field-effect transistors (OFETs), and drug development.

One of the most compelling aspects of 5-Bromo-2,2'-bithiophene-5'-carbonitrile is its role in the synthesis of conjugated polymers and small molecules. These materials are crucial for next-generation electronic devices due to their ability to conduct charge efficiently. The bromine atom at the 5-position allows for further functionalization via cross-coupling reactions such as Suzuki or Stille couplings, enabling the creation of complex molecular architectures. Similarly, the nitrile group can undergo various transformations, including reduction to an amine or hydrolysis to a carboxylic acid, providing additional synthetic flexibility.

Recent studies have highlighted the compound's utility in the development of novel organic semiconductors. For instance, researchers have demonstrated its incorporation into π-conjugated polymers that exhibit high charge carrier mobility and excellent film-forming properties. These polymers have shown promise in applications such as flexible electronics and photovoltaic devices. The structural features of 5-Bromo-2,2'-bithiophene-5'-carbonitrile contribute to its ability to form stable π-stacking interactions, which are essential for efficient charge transport in these materials.

In addition to its applications in materials science, 5-Bromo-2,2'-bithiophene-5'-carbonitrile has garnered attention in pharmaceutical research. Bithiophene derivatives are known for their biological activity and have been investigated as potential therapeutic agents. The nitrile group in this compound can be further modified to introduce pharmacophores that interact with biological targets. For example, it can be converted into a carboxylic acid or an amide, which are common functional groups in drug molecules. The bromine substituent also facilitates further derivatization, allowing for the creation of diverse chemical libraries for drug discovery.

The synthesis of 5-Bromo-2,2'-bithiophene-5'-carbonitrile typically involves multi-step organic reactions starting from commercially available thiophene precursors. A common synthetic route includes bromination followed by cyanation or vice versa, depending on the desired regioselectivity. Advanced catalytic methods have been employed to improve yield and selectivity in these reactions. For instance, palladium-catalyzed cross-coupling reactions have been utilized to introduce bromine or nitrile groups with high precision.

The compound's stability under various conditions makes it suitable for industrial-scale production and application. It can be stored under inert atmospheres at ambient temperatures without significant degradation, ensuring its reliability for large-scale synthesis and processing. Furthermore, its solubility in common organic solvents allows for easy handling and integration into various chemical systems.

From an industrial perspective, 5-Bromo-2,2'-bithiophene-5'-carbonitrile represents a cost-effective intermediate for producing high-performance materials. Its ability to undergo multiple functionalizations without significant loss of yield makes it an attractive choice for manufacturers seeking efficient synthetic routes. As demand for advanced electronic devices continues to grow, compounds like this are expected to play a crucial role in meeting industry needs.

In conclusion,5-Bromo-2,2'-bithiophene-5'-carbonitrile (CAS No. 176787-96-5) is a multifunctional compound with broad applications in organic electronics and pharmaceutical research. Its unique structural features enable diverse chemical modifications, making it a valuable tool for synthesizing advanced materials and drug candidates. With ongoing research exploring new applications and synthetic methodologies,this compound is poised to remain at the forefront of innovation in multiple scientific disciplines.

• 4805-22-5(5,5’-Dibromo-2,2-bithiophene)
• 647835-93-6(2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-Sexithiophene, 5,5'''''-dibromo-)
• 415718-60-4(4-(5-Bromothiophen-2-yl)benzonitrile)
• 3480-11-3(5-Bromo-2,2-bithiophene 96%)
• 146796-00-1(2,2'-Bithiophene, 5-bromo-5'-methyl-)
• 94581-95-0(2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene)
• 2160-62-5(5-Bromothiophene-2-carbonitrile)
• 144153-60-6(2,2':5',2'':5'',2''':5''',2''''-Quinquethiophene, 5,5''''-dibromo-)
• 351066-58-5(2,2':5',2''-Terthiophene, 5-bromo-5''-methyl-)
• 98057-08-0(5,5''-Dibromo-2,2':5',2''-terthiophene)