Cas no 1219628-58-6 (5-Acetylthiophene-3-boronic acid pinacol ester)

5-Acetylthiophene-3-boronic acid pinacol ester is a high-purity boronic ester derivative commonly employed in Suzuki-Miyaura cross-coupling reactions. Its thiophene backbone and acetyl functional group enhance reactivity and selectivity in forming carbon-carbon bonds, particularly in heterocyclic systems. The pinacol ester moiety improves stability, facilitating handling and storage under ambient conditions. This compound is particularly useful in pharmaceutical and materials science research, where precise functionalization of thiophene-based scaffolds is required. Its compatibility with a wide range of reaction conditions and substrates makes it a versatile intermediate for synthesizing complex organic molecules. Typical applications include the development of conjugated polymers, agrochemicals, and bioactive compounds.
5-Acetylthiophene-3-boronic acid pinacol ester structure
1219628-58-6 structure
Product Name:5-Acetylthiophene-3-boronic acid pinacol ester
CAS No:1219628-58-6
MF:C12H17BO3S
MW:252.137582540512
MDL:MFCD12198153
CID:4687081
Update Time:2025-10-31

5-Acetylthiophene-3-boronic acid pinacol ester Chemical and Physical Properties

Names and Identifiers

    • 5-Acetylthiophene-3-boronic acid pinacol ester
    • 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethan-1-one
    • 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethanone
    • MDL: MFCD12198153
    • Inchi: 1S/C12H17BO3S/c1-8(14)10-6-9(7-17-10)13-15-11(2,3)12(4,5)16-13/h6-7H,1-5H3
    • InChI Key: LIUCDZGQETVONG-UHFFFAOYSA-N
    • SMILES: S1C(C(C)=O)=CC(B2OC(C)(C)C(C)(C)O2)=C1

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 314
  • Topological Polar Surface Area: 63.8

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5-Acetylthiophene-3-boronic acid pinacol ester Related Literature

Additional information on 5-Acetylthiophene-3-boronic acid pinacol ester

Comprehensive Overview of 5-Acetylthiophene-3-boronic acid pinacol ester (CAS No. 1219628-58-6)

5-Acetylthiophene-3-boronic acid pinacol ester (CAS No. 1219628-58-6) is a highly versatile boronic acid derivative widely utilized in organic synthesis, pharmaceutical research, and material science. This compound belongs to the class of thiophene-based boronic esters, which are pivotal intermediates in Suzuki-Miyaura cross-coupling reactions. Its unique structure, featuring an acetyl group and a pinacol boronate moiety, makes it a valuable building block for constructing complex molecules.

The growing demand for 5-Acetylthiophene-3-boronic acid pinacol ester is driven by its applications in drug discovery, particularly in the development of kinase inhibitors and anticancer agents. Researchers are increasingly exploring its potential in targeted therapy, aligning with the current trend of personalized medicine. Additionally, its role in OLED materials and organic electronics has garnered attention, as the industry seeks sustainable alternatives to conventional materials.

One of the most frequently asked questions about 5-Acetylthiophene-3-boronic acid pinacol ester revolves around its stability and storage conditions. This compound is typically stored under inert conditions at low temperatures to prevent degradation. Another common query concerns its solubility, which is excellent in organic solvents like THF, DMSO, and dichloromethane, making it ideal for various synthetic applications.

In the context of green chemistry, 5-Acetylthiophene-3-boronic acid pinacol ester stands out due to its compatibility with catalytic processes that minimize waste. This aligns with the global push toward sustainable synthesis and eco-friendly manufacturing. Furthermore, its use in bioconjugation and proteomics highlights its relevance in cutting-edge biomedical research.

The synthetic routes for 5-Acetylthiophene-3-boronic acid pinacol ester often involve Pd-catalyzed borylation or transesterification of corresponding boronic acids. These methods are well-documented in literature, ensuring reproducibility for industrial and academic labs. Its high purity and consistent performance make it a preferred choice for high-throughput screening and combinatorial chemistry.

As the scientific community continues to explore boron-containing compounds, 5-Acetylthiophene-3-boronic acid pinacol ester remains a focal point due to its structural adaptability and functional diversity. Whether in small-molecule drug development or advanced material engineering, this compound exemplifies the intersection of innovation and practicality.

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