• 1. Synthesis, crystal structures and electronic properties of imidazoline nitroxide radicals bearing active groups in electropolymerisation
  Eugenio Coronado,Carlos Giménez-Saiz,Mael Nicolas,Francisco M. Romero,Eduard Rusanov,Helen Stoeckli-Evans New J. Chem. 2003 27 490

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives

Introduction to 4-(Thiophen-3-yl)benzaldehyde (CAS No. 157730-74-0)

4-(Thiophen-3-yl)benzaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 157730-74-0, is a significant organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and materials science. This aromatic aldehyde, featuring a benzaldehyde moiety linked to a thiophene ring, exhibits unique structural and chemical properties that make it a valuable intermediate in synthetic chemistry. The presence of both electron-donating and withdrawing groups in its molecular structure imparts distinct reactivity, enabling its application in diverse chemical transformations.

The compound's molecular formula, C₁₀H₆O₂S, reflects its composition of carbon, hydrogen, oxygen, and sulfur atoms. The thiophene ring, a five-membered heterocyclic aromatic ring containing sulfur, contributes to the compound's stability and electronic characteristics. This structural motif is widely recognized for its role in medicinal chemistry due to its ability to interact with biological targets, often enhancing the pharmacological activity of associated molecules.

In recent years, 4-(Thiophen-3-yl)benzaldehyde has been extensively studied for its potential applications in drug development. Its aldehyde group serves as a versatile handle for further functionalization, allowing chemists to construct more complex molecules through condensation reactions, such as Schiff base formations. These derivatives have shown promise in various therapeutic areas, including anti-inflammatory, antimicrobial, and anticancer applications. The combination of the benzaldehyde and thiophene moieties provides a scaffold that can be modulated to optimize biological activity and pharmacokinetic properties.

One of the most compelling aspects of 4-(Thiophen-3-yl)benzaldehyde is its role as a key intermediate in the synthesis of biologically active compounds. Researchers have leveraged its reactivity to develop novel heterocyclic derivatives with enhanced binding affinity to target proteins. For instance, studies have demonstrated its utility in generating small-molecule inhibitors that modulate enzyme activity relevant to neurological disorders. The thiophene ring's ability to engage with π-stacking interactions and hydrophobic pockets in proteins further enhances the design of high-affinity ligands.

The compound's significance extends beyond pharmaceutical applications into the realm of materials science. Its aromatic structure and conjugated system make it a candidate for use in organic electronics, particularly in the development of organic light-emitting diodes (OLEDs) and photovoltaic devices. The thiophene moiety's electron-donating properties contribute to improved charge transport characteristics, which are critical for efficient device performance. Additionally, derivatives of 4-(Thiophen-3-yl)benzaldehyde have been explored as precursors for conductive polymers and liquid crystals.

Recent advancements in synthetic methodologies have further expanded the utility of 4-(Thiophen-3-yl)benzaldehyde. Transition-metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Stille couplings, have enabled the introduction of diverse substituents onto both the benzaldehyde and thiophene components. These techniques have facilitated the creation of libraries of structurally diverse compounds for high-throughput screening, accelerating the discovery process in drug discovery programs.

The compound's stability under various reaction conditions has also been a subject of interest. Studies have shown that 4-(Thiophen-3-yl)benzaldehyde maintains its integrity under mild conditions while still participating efficiently in multiple synthetic steps. This balance between reactivity and stability makes it an attractive choice for multi-step syntheses where maintaining intermediate purity is crucial.

In conclusion,4-(Thiophen-3-yl)benzaldehyde (CAS No. 157730-74-0) is a multifaceted compound with broad applications across pharmaceuticals and materials science. Its unique structural features enable diverse chemical modifications, making it a valuable building block for developing novel therapeutics and advanced materials. As research continues to uncover new synthetic strategies and biological functions,4-(Thiophen-3-yl)benzaldehyde is poised to remain at the forefront of chemical innovation.

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