Cas no 1515103-64-6 (1-(5-iodothiophen-3-yl)ethanone)

1-(5-Iodothiophen-3-yl)ethanone is a versatile heterocyclic compound featuring a thiophene ring substituted with an acetyl group at the 3-position and an iodine atom at the 5-position. This structure makes it a valuable intermediate in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and functional materials. The iodine substituent enhances its reactivity in cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling efficient derivatization. The acetyl group offers further functionalization potential through condensation or reduction reactions. Its well-defined reactivity and stability under standard conditions make it a reliable building block for constructing complex molecular architectures. Suitable for research and industrial applications, this compound is typically handled under inert conditions to preserve its integrity.
1-(5-iodothiophen-3-yl)ethanone structure
1515103-64-6 structure
Product Name:1-(5-iodothiophen-3-yl)ethanone
CAS No:1515103-64-6
MF:C6H5IOS
MW:252.072772741318
CID:5251315
Update Time:2025-08-05

1-(5-iodothiophen-3-yl)ethanone Chemical and Physical Properties

Names and Identifiers

    • 1-(5-iodothiophen-3-yl)ethanone
    • Inchi: 1S/C6H5IOS/c1-4(8)5-2-6(7)9-3-5/h2-3H,1H3
    • InChI Key: VSIILWVOZVIREX-UHFFFAOYSA-N
    • SMILES: C(C1=CSC(=C1)I)(=O)C

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Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Enamine
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Enamine
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Additional information on 1-(5-iodothiophen-3-yl)ethanone

Introduction to 1-(5-iodothiophen-3-yl)ethanone (CAS No. 1515103-64-6)

1-(5-iodothiophen-3-yl)ethanone, identified by the chemical identifier CAS No. 1515103-64-6, is a significant compound in the realm of organic synthesis and pharmaceutical research. This compound belongs to the class of thiophene derivatives, which have garnered considerable attention due to their diverse biological activities and structural versatility. The presence of an iodine atom at the 5-position of the thiophene ring and a ketone functional group at the 3-position enhances its reactivity, making it a valuable intermediate in synthetic chemistry.

The structural motif of 1-(5-iodothiophen-3-yl)ethanone combines the aromatic stability of the thiophene ring with the electrophilic nature of the ketone group. This unique combination allows it to participate in a variety of chemical transformations, including cross-coupling reactions, nucleophilic additions, and condensation reactions. These properties make it particularly useful in the synthesis of more complex molecules, such as drug candidates and functional materials.

In recent years, there has been a growing interest in thiophene derivatives due to their potential applications in pharmaceuticals, agrochemicals, and materials science. The iodine substituent on the thiophene ring serves as an excellent handle for palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Heck couplings. These reactions are fundamental tools in modern organic synthesis, enabling the construction of carbon-carbon bonds with high selectivity and yield.

One of the most compelling aspects of 1-(5-iodothiophen-3-yl)ethanone is its utility in the development of novel therapeutic agents. Thiophene derivatives have been shown to exhibit a wide range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The structural flexibility of these compounds allows for the facile introduction of various pharmacophores, making them ideal candidates for drug discovery efforts. For instance, modifications at the 2- and 3-positions of the thiophene ring can significantly alter the biological profile of the molecule, leading to enhanced efficacy or improved selectivity.

Recent studies have highlighted the role of 1-(5-iodothiophen-3-yl)ethanone in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways and are often implicated in diseases such as cancer. By designing molecules that specifically target kinase activity, researchers can develop drugs that disrupt aberrant signaling pathways. The ketone group in 1-(5-iodothiophen-3-yl)ethanone provides a scaffold for further functionalization, allowing for the creation of potent inhibitors with high binding affinity.

The compound has also found applications in materials science, particularly in the development of organic electronic devices. Thiophene-based polymers and small molecules are widely used in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (OFETs). The iodine substituent facilitates further derivatization, enabling the tuning of electronic properties such as charge transportability and luminescence efficiency. This makes 1-(5-iodothiophen-3-yl)ethanone a valuable building block for constructing advanced materials with tailored functionalities.

The synthesis of 1-(5-iodothiophen-3-yl)ethanone typically involves multi-step procedures starting from commercially available precursors such as 5-bromothiophene or 5-chlorothiophene. Palladium-catalyzed cross-coupling reactions are commonly employed to introduce the iodine atom at the 5-position, followed by oxidation to yield the ketone functionality. These synthetic routes highlight the importance of 1-(5-iodothiophen-3-yl)ethanone as a versatile intermediate that can be readily modified to suit specific synthetic needs.

In conclusion,1-(5-iodothiophen-3-ylenthanone (CAS No. 1515103-64-6) is a multifaceted compound with significant applications in pharmaceutical research and materials science. Its unique structural features make it an excellent candidate for further chemical manipulation, enabling access to a diverse array of biologically active molecules and advanced functional materials. As research continues to uncover new applications for thiophene derivatives,1-(5-iothiophen -3-ylenthanone is poised to remain a cornerstone in synthetic chemistry.

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