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  • 2-Chloropyridine-5-boronic acid

  • 2-Chloropyridine-5-boronic acid

    Catalog Number
    ACM444120916-1
    CAS Number
    444120-91-6
    Product Name
    2-Chloropyridine-5-boronic acid
    Structure
    Category
    Salt
    Synonyms
    2-CHLORO-5-PYRIDYL BORONIC ACID;2-CHLORO-5-PYRIDINEBORONIC ACID;2-CHLOROPYRIDIN-5-YLBORONIC ACID;2-CHLOROPYRIDINE-5-BORONIC ACID;(6-CHLOROPYRIDIN-3-YL)BORONIC ACID;6-CHLOROPYRIDIN-3-YL-3-BORONIC ACID;6-CHLOROPYRIDINE-3-BORONIC ACID;6-CHLORO-3-PYRIDINYLBOR
    IUPAC Name
    (6-chloropyridin-3-yl)boronic acid
    Molecular Weight
    157.36g/mol
    Molecular Formula
    C5H5BClNO2
    Canonical SMILES
    B(C1=CN=C(C=C1)Cl)(O)O
    InChI
    InChI=1S/C5H5BClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H
    InChI Key
    WPAPNCXMYWRTTL-UHFFFAOYSA-N
    Purity
    98%
    Application
    2-Chloropyridine-5-boronic acid is a versatile white to off-white solid utilized in a variety of chemical synthesis applications. It plays a crucial role in the formation of biologically significant compounds, such as 3-arylcoumarins, through the Suzuki reaction with 3-chlorocoumarin. Additionally, it serves as a key substrate in the synthesis of 11-(pyridinylphenyl)steroids, which exhibit a progesterone agonist/antagonist profile. The compound is also instrumental in the preparation of α-secondary and tertiary pyridines by reacting with pyridotriazoles, as well as in the palladium-catalyzed α-arylation of saturated cyclic amines and N-methyl amines, demonstrating its importance in facilitating advanced chemical transformations.
    Complexity
    114
    Covalently-Bonded Unit Count
    1
    Exact Mass
    157.010186g/mol
    Formal Charge
    0
    Heavy Atom Count
    10
    Monoisotopic Mass
    157.010186g/mol
    Rotatable Bond Count
    1
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