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  • 4-Iodophenylboronic acid

  • 4-Iodophenylboronic acid

    Catalog Number
    ACM5122996
    CAS Number
    5122-99-6
    Product Name
    4-Iodophenylboronic acid
    Structure
    Category
    Salt
    Synonyms
    4-IODOBENZENEBORONIC ACID;4-IODOPHENYLBORONIC ACID;RARECHEM AH PB 0035;P-IODOPHENYLBORONIC ACID;4-Iodophenylboronic acid,97%;p-IodophenylboromcAcid;4-Iodophenylboronic acid ,98%;4-Iodophenylboronic
    IUPAC Name
    (4-iodophenyl)boronic acid
    Molecular Weight
    247.83g/mol
    Molecular Formula
    C6H6BIO2
    Canonical SMILES
    B(C1=CC=C(C=C1)I)(O)O
    InChI
    InChI=1S/C6H6BIO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
    InChI Key
    PELJYVULHLKXFF-UHFFFAOYSA-N
    Purity
    97%
    Application
    4-Iodophenylboronic acid is a versatile white crystalline powder that serves as a key reagent in a variety of advanced chemical reactions. It plays a crucial role in copper-mediated ligandless aerobic fluoroalkylation and palladium-catalyzed aerobic oxidative cross-coupling reactions. Its utility extends to the realm of recyclable magnetic-nanoparticle-supported palladium catalysis in Suzuki coupling reactions, offering efficient oxidative hydroxylation with copper catalysts. Moreover, it is involved in ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling and homocoupling processes using gold salts as catalysts. Additionally, 4-Iodophenylboronic acid is employed in ruthenium-catalyzed cross-coupling and CuI-catalyzed Suzuki coupling reactions. It supports complex transformations such as palladium-catalyzed domino Heck-Mizoroki/Suzuki-Miyaura reactions and facilitates manganese triacetate-mediated radical additions of arylboronic acids to alkenes. Beyond these applications, this reagent is integral to the preparation of pleuromutilin derivatives, aimed at ribosomal binding and antibacterial activity via "Click Chemistry," as well as in the development of liquid crystalline polyacetylene derivatives.
    Complexity
    102
    Covalently-Bonded Unit Count
    1
    Exact Mass
    247.95056g/mol
    Formal Charge
    0
    Heavy Atom Count
    10
    MeSH Entry Terms
    4-iodophenylboronic acid
    Monoisotopic Mass
    247.95056g/mol
    Rotatable Bond Count
    1
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