Cas no 1322001-30-8 ((6-formylpyridin-3-yl)boronic Acid)

(6-Formylpyridin-3-yl)boronic acid is a versatile boronic acid derivative featuring both a formyl group and a boronic acid functionality on a pyridine scaffold. This bifunctional structure makes it a valuable intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex heterocyclic compounds. The formyl group offers additional reactivity for further derivatization, such as condensation or reduction, enhancing its utility in pharmaceutical and agrochemical applications. Its stability under typical reaction conditions and compatibility with various protecting groups contribute to its broad applicability in organic synthesis. The compound is particularly useful in constructing pyridine-based frameworks for drug discovery and materials science.
(6-formylpyridin-3-yl)boronic Acid structure
1322001-30-8 structure
Product Name:(6-formylpyridin-3-yl)boronic Acid
CAS No:1322001-30-8
MF:C6H6BNO3
MW:150.927741527557
MDL:MFCD06409954
CID:1229982
PubChem ID:45073592
Update Time:2025-05-25

(6-formylpyridin-3-yl)boronic Acid Chemical and Physical Properties

Names and Identifiers

    • (6-formylpyridin-3-yl)boronic Acid
    • AKOS006292837
    • 2-FORMYLPYRIDINE-5-BORONIC ACID
    • 6-formylpyridin-3-yl boronic acid
    • 6-FORMYLPYRIDINE-3-BORONIC ACID
    • KB-170530
    • AB23829
    • PubChem2089
    • AKOS006292837; 2-FORMYLPYRIDINE-5-BORONIC ACID; 6-formylpyridin-3-yl boronic acid; 6-FORMYLPYRIDINE-3-BORONIC ACID; KB-170530; AB23829; PubChem2089;
    • 6-formylpyridin-3-ylboronic acid
    • 1322001-30-8
    • SCHEMBL904470
    • (6-FORMYLPYRIDIN-3-YL)BORONICACID
    • EN300-2984722
    • (6-formylpyridin-3-yl) boronic acid
    • CS-0173798
    • QZLRSNPWLRXKTB-UHFFFAOYSA-N
    • DB-009961
    • A849354
    • MFCD06409954
    • MDL: MFCD06409954
    • Inchi: 1S/C6H6BNO3/c9-4-6-2-1-5(3-8-6)7(10)11/h1-4,10-11H
    • InChI Key: QZLRSNPWLRXKTB-UHFFFAOYSA-N
    • SMILES: OB(C1=CN=C(C=O)C=C1)O

Computed Properties

  • Exact Mass: 151.0440732g/mol
  • Monoisotopic Mass: 151.0440732g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 142
  • 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: 70.4?2

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Additional information on (6-formylpyridin-3-yl)boronic Acid

Recent Advances in the Application of (6-Formylpyridin-3-yl)boronic Acid (CAS: 1322001-30-8) in Chemical Biology and Drug Discovery

(6-Formylpyridin-3-yl)boronic acid (CAS: 1322001-30-8) is a versatile boronic acid derivative that has recently gained significant attention in chemical biology and pharmaceutical research. This compound, characterized by its formyl and boronic acid functional groups, serves as a critical building block in the synthesis of bioactive molecules and as a key intermediate in Suzuki-Miyaura cross-coupling reactions. Recent studies have highlighted its potential in targeted drug delivery, enzyme inhibition, and as a molecular probe for detecting biomolecules.

One of the most notable applications of (6-formylpyridin-3-yl)boronic acid is its role in the development of proteolysis-targeting chimeras (PROTACs). PROTACs are bifunctional molecules designed to degrade specific disease-causing proteins by recruiting ubiquitin ligases. The boronic acid moiety in this compound facilitates the binding to specific amino acid residues, enhancing the selectivity and efficacy of PROTACs. Recent research published in the Journal of Medicinal Chemistry demonstrated its utility in designing PROTACs targeting oncogenic proteins, showing promising results in preclinical models of cancer.

In addition to its use in PROTACs, (6-formylpyridin-3-yl)boronic acid has been explored as a sensor for glucose and other diols. The boronic acid group forms reversible covalent bonds with diols, making it an excellent candidate for developing non-enzymatic glucose sensors. A 2023 study in ACS Sensors reported a novel biosensor utilizing this compound, which exhibited high sensitivity and selectivity for glucose detection in physiological conditions, paving the way for improved diabetes management technologies.

Furthermore, the compound's unique reactivity has been leveraged in the synthesis of complex heterocycles, which are prevalent in many FDA-approved drugs. A recent publication in Organic Letters detailed a novel catalytic system using (6-formylpyridin-3-yl)boronic acid to facilitate the construction of pyridine-based scaffolds, which are essential in antiviral and anti-inflammatory drug development. The study highlighted the compound's ability to act as a dual-functional reagent, serving both as a substrate and a catalyst in multicomponent reactions.

Despite its promising applications, challenges remain in optimizing the stability and bioavailability of (6-formylpyridin-3-yl)boronic acid-derived compounds. Researchers are actively investigating strategies such as prodrug approaches and nanoparticle encapsulation to address these limitations. A 2024 review in Chemical Society Reviews summarized recent advancements in this area, emphasizing the need for interdisciplinary collaboration to fully realize the potential of this compound in translational medicine.

In conclusion, (6-formylpyridin-3-yl)boronic acid (CAS: 1322001-30-8) represents a valuable tool in modern chemical biology and drug discovery. Its diverse applications, from targeted protein degradation to biosensing, underscore its importance in advancing therapeutic and diagnostic technologies. Future research should focus on overcoming current limitations and exploring novel applications to further expand its utility in the biomedical field.

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