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  • (4-Aminophenyl)boronic acid pinacol ester

  • (4-Aminophenyl)boronic acid pinacol ester

    Catalog Number
    ACM214360733-1
    CAS Number
    214360-73-3
    Product Name
    (4-Aminophenyl)boronic acid pinacol ester
    Structure
    Category
    Salt
    Synonyms
    2-(4-AMINOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-Y)ANILINE;4-AMINOPHENYLBORONIC ACID PINACOLATE;4-AMINOPHENYLBORONIC ACID PINACOL CYCLIC ESTER;4-AM
    IUPAC Name
    4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
    Molecular Weight
    219.09
    Molecular Formula
    C12H18BNO2
    Canonical SMILES
    B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N
    InChI Key
    ZANPJXNYBVVNSD-UHFFFAOYSA-N
    Boiling Point
    340ºC at 760mmHg
    Melting Point
    165-170ºC
    Flash Point
    159.4ºC
    Purity
    98%
    Density
    1.05g/cm³
    Appearance
    almost white to light beige crystalline powder
    Application
    (4-Aminophenyl)boronic acid pinacol ester, an almost white to light beige crystalline powder, serves as a versatile reagent in various chemical syntheses and analytical applications. It is instrumental in the preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones through Pd-catalyzed Suzuki-Miyaura cross-coupling with iodochromones. Additionally, it facilitates the detection of mercury(II) via fluorometry using fluorogenic indicators that utilize energy transfer from pentaquinone to rhodamine. This compound is also critical in rhodium-catalyzed amination reactions and in palladium-catalyzed Suzuki cross-coupling, which are used to synthesize potential antitubercular and antimicrobial agents. Furthermore, (4-Aminophenyl)boronic acid pinacol ester is used in the development of hexaphenylbenzene derivatives as bioprobes and multichannel keypad systems, as well as in the production of pyromellitic diimide-based polymer matrices for solution-processable n-channel field-effect transistors. It also aids in the creation of alternating copolymers of oligoarylenes and naphthalene bisimides, which function as low band-gap semiconductors exhibiting notable electrochemical and spectroelectrochemical properties. Finally, it plays a role in generating γ-secretase modulators aimed at mitigating amyloid β formation.
    Exact Mass
    219.14300
    Hazard Statements
    Xi:Irritant
    Safety Description
    S26-S37/39
    WGK Germany
    3
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