Cas no 81557-66-6 (1-(2-Chlorothiophen-3-yl)ethanone)

1-(2-Chlorothiophen-3-yl)ethanone is a chlorinated thiophene derivative with a ketone functional group, widely used as a key intermediate in organic synthesis and pharmaceutical manufacturing. Its structural features, including the reactive acetyl group and chlorine substitution, make it valuable for constructing heterocyclic compounds, agrochemicals, and active pharmaceutical ingredients (APIs). The compound exhibits high purity and stability, ensuring reliable performance in reactions such as nucleophilic substitutions or condensations. Its well-defined molecular structure allows for precise functionalization, facilitating the development of complex molecules. Suitable for controlled laboratory and industrial-scale applications, it is handled under standard safety protocols due to its moderate reactivity.
1-(2-Chlorothiophen-3-yl)ethanone structure
81557-66-6 structure
Product Name:1-(2-Chlorothiophen-3-yl)ethanone
CAS No:81557-66-6
MF:C6H5ClOS
MW:160.621299505234
CID:4817259
Update Time:2025-06-07

1-(2-Chlorothiophen-3-yl)ethanone Chemical and Physical Properties

Names and Identifiers

    • 1-(2-chlorothiophen-3-yl)ethanone
    • 3-acetyl chlorothiophene
    • Ethanone, 1-(2-chloro-3-thienyl)-
    • AB72529
    • 1-(2-CHLOROTHIEN-3-YL)ETHANONE
    • 1-(2-Chlorothiophen-3-yl)ethanone
    • Inchi: 1S/C6H5ClOS/c1-4(8)5-2-3-9-6(5)7/h2-3H,1H3
    • InChI Key: ZLKHBAWNFOPUOZ-UHFFFAOYSA-N
    • SMILES: ClC1=C(C=CS1)C(C)=O

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 126
  • XLogP3: 2.2
  • Topological Polar Surface Area: 45.3

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Additional information on 1-(2-Chlorothiophen-3-yl)ethanone

Professional Introduction to 1-(2-Chlorothiophen-3-yl)ethanone (CAS No. 81557-66-6)

1-(2-Chlorothiophen-3-yl)ethanone, identified by its Chemical Abstracts Service (CAS) number 81557-66-6, is a significant compound in the field of organic chemistry and pharmaceutical research. This heterocyclic ketone features a thiophene ring substituted with a chlorine atom at the 2-position and an acetyl group at the 3-position, making it a versatile intermediate in synthetic chemistry. The unique structural properties of this compound have garnered attention for its potential applications in drug development, agrochemical synthesis, and material science.

The molecular structure of 1-(2-Chlorothiophen-3-yl)ethanone consists of a thiophene core, which is a five-membered aromatic ring containing sulfur, fused with a benzene-like system. The presence of the chlorine atom at the 2-position enhances its reactivity, allowing for various functionalization strategies. This reactivity makes it a valuable building block for constructing more complex molecules, particularly in medicinal chemistry. The ketone group at the 3-position further contributes to its versatility, enabling reactions such as condensation, oxidation, and reduction.

In recent years, 1-(2-Chlorothiophen-3-yl)ethanone has been extensively studied for its pharmacological properties. Researchers have explored its potential as a precursor in the synthesis of bioactive molecules, including antimicrobial, anti-inflammatory, and anticancer agents. The thiophene scaffold is known for its presence in numerous natural products and pharmaceuticals, owing to its ability to interact with biological targets effectively. The chloro-substituted thiophene derivative has shown promise in modulating enzyme activity and receptor binding, making it a focal point in drug discovery efforts.

One of the most compelling aspects of 1-(2-Chlorothiophen-3-yl)ethanone is its role in developing novel therapeutic agents. For instance, studies have demonstrated its utility in creating small-molecule inhibitors targeting specific disease pathways. The chlorine atom at the 2-position allows for selective interactions with biological macromolecules, which is crucial for achieving high specificity in drug design. Furthermore, the ketone group can be further modified to introduce additional functional groups, enhancing the compound's pharmacological profile.

The synthesis of 1-(2-Chlorothiophen-3-yl)ethanone involves multi-step organic reactions that highlight the compound's synthetic importance. Common synthetic routes include Friedel-Crafts acylation of chlorothiophene derivatives followed by functional group transformations. These synthetic strategies not only showcase the compound's reactivity but also demonstrate its feasibility as an intermediate in large-scale production. The ability to efficiently synthesize this compound under controlled conditions is essential for its application in industrial and academic research settings.

The pharmacological activity of 1-(2-Chlorothiophen-3-yl)ethanone has been investigated through various experimental approaches. In vitro studies have revealed its potential as an inhibitor of certain kinases and enzymes implicated in cancer progression. Additionally, preliminary in vivo studies suggest that derivatives of this compound may exhibit significant therapeutic effects without notable side effects. These findings underscore the importance of further exploration into its pharmacological properties and potential clinical applications.

The versatility of 1-(2-Chlorothiophen-3-yl)ethanone extends beyond pharmaceutical applications. In agrochemical research, this compound has been explored as a precursor for developing novel pesticides and herbicides. Its structural features allow for interactions with biological targets in pests and weeds while maintaining low toxicity to non-target organisms. This makes it a promising candidate for creating environmentally friendly agrochemical solutions.

The material science applications of 1-(2-Chlorothiophen-3-yl)ethanone are also noteworthy. Due to its aromatic nature and functional groups, this compound can be incorporated into polymers and materials with enhanced electronic properties. Researchers have investigated its use in developing organic semiconductors and light-emitting diodes (OLEDs). The ability to tailor the electronic characteristics of materials using such heterocyclic compounds opens up new possibilities in nanotechnology and advanced material design.

In conclusion, 1-(2-Chlorothiophen-3-yl)ethanone(CAS No. 81557-66-6) is a multifaceted compound with significant implications across various scientific disciplines. Its unique structural features make it a valuable intermediate in synthetic chemistry, while its pharmacological properties position it as a key player in drug discovery efforts. Furthermore, its potential applications in agrochemicals and material science highlight its broad utility. As research continues to uncover new aspects of this compound's properties and applications, it will undoubtedly remain a subject of great interest and innovation.

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