Cas no 1218791-33-3 (2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester)

2-Acetamido-5-acrylamidophenylboronic acid pinacol ester is a boronic acid derivative featuring both acetamido and acrylamido functional groups. The pinacol ester moiety enhances stability, making it suitable for applications requiring controlled reactivity, such as Suzuki-Miyaura cross-coupling reactions. The acrylamido group allows for further functionalization, enabling its use in polymer chemistry or bioconjugation. This compound is particularly valuable in medicinal chemistry and materials science due to its dual reactivity, offering versatility in synthesizing complex molecules. Its stability under ambient conditions and compatibility with aqueous and organic solvents further broaden its utility in research and industrial applications.
2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester structure
1218791-33-3 structure
Product Name:2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester
CAS No:1218791-33-3
MF:C17H23BN2O4
MW:330.186524629593
MDL:MFCD12546617
CID:828310
Update Time:2026-04-29

2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester Chemical and Physical Properties

Names and Identifiers

    • N-(4-Acetamido-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylamide
    • 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester
    • N-[4-acetamido-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]prop-2-enamide
    • MDL: MFCD12546617

Computed Properties

  • Exact Mass: 330.17500
  • Monoisotopic Mass: 330.175
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 24
  • Rotatable Bond Count: 4
  • Complexity: 505
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 76.7A^2

Experimental Properties

  • PSA: 83.64000
  • LogP: 3.36770

2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester Pricemore >>

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Additional information on 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester

Research Update on 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester (CAS: 1218791-33-3)

2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester (CAS: 1218791-33-3) is a boronic acid derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. This compound, characterized by its unique acrylamido and boronic ester functionalities, has been explored for its role in targeted therapies, particularly in the context of cancer treatment and enzyme inhibition. Recent studies have highlighted its utility as a versatile building block in the synthesis of bioactive molecules and as a probe for studying protein-ligand interactions.

Recent research has focused on the mechanistic insights into the compound's interactions with biological targets. A study published in the Journal of Medicinal Chemistry (2023) demonstrated that 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester exhibits selective binding affinity towards certain serine proteases, which are implicated in various pathological conditions, including cancer metastasis and inflammatory diseases. The study utilized X-ray crystallography and molecular docking simulations to elucidate the binding mode of the compound, revealing key interactions between the boronic ester moiety and the active site residues of the target enzyme.

In addition to its enzymatic inhibition properties, this compound has been investigated for its potential in targeted drug delivery systems. A recent preprint on bioRxiv (2024) reported the development of a polymer-drug conjugate incorporating 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester as a linker. The conjugate demonstrated enhanced stability and controlled release of the therapeutic payload in response to specific physiological conditions, such as the acidic microenvironment of tumor tissues. This approach holds promise for improving the pharmacokinetics and reducing off-target effects of conventional chemotherapeutic agents.

Further advancements in the synthetic methodology for this compound have also been reported. A study in Organic Letters (2023) described an optimized route for the large-scale synthesis of 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester, addressing previous challenges related to yield and purity. The new protocol employs a palladium-catalyzed borylation reaction, which offers improved efficiency and scalability, making the compound more accessible for preclinical and clinical studies.

Despite these promising developments, challenges remain in the clinical translation of this compound. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be thoroughly investigated. Ongoing research is exploring structural modifications to enhance the pharmacological profile of 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester, while retaining its desirable biological activities.

In conclusion, 2-Acetamido-5-acrylamidophenylboronic acid, pinacol ester (CAS: 1218791-33-3) represents a promising scaffold in medicinal chemistry with diverse applications. Continued research into its mechanism of action, synthetic optimization, and therapeutic potential will be crucial for its advancement into clinical applications. The compound's unique chemical properties and biological activities position it as a valuable tool for both basic research and drug development efforts.

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