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    388116-27-6

    Catalog No. EBD50931

    CAS 388116-27-6

    Name 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    Basic Information

    Synonyms: Indole-4-boronicacid,pinacolester 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Indole-4-boronicacidpinacolester

    Molecular Formula: C14H18BNO2

    Molecular Weight: 243.11

    MDL Number: MFCD08689896

    Categories: Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

    Product Description:
    4-Indolylboronic acid pinacol ester is an organoboron compound featuring an indole ring system protected by a pinacol ester group. This structural motif makes it a stable and versatile building block, commonly referred to as 4-indoleboronic acid pinacol ester or 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole. Its primary application is in organic synthesis, particularly in transition-metal-catalyzed cross-coupling reactions such as the Suzuki-Miyaura reaction. The boronic ester functionality allows for the efficient introduction of the 4-indolyl moiety into more complex molecular architectures. This makes it a valuable intermediate in medicinal chemistry for the synthesis of drug candidates and biologically active molecules that contain the indole scaffold, a privileged structure found in many pharmaceuticals. As a protected boronic acid derivative, it offers improved stability and handling compared to the free boronic acid, facilitating its use in multi-step synthetic sequences. It is a standard reagent available from major chemical suppliers for research and development purposes.
    Physical Properties

    Melting Point: 168-173 °C

    Boiling Point: 395.997 °C at 760 mmHg

    Flash Point: 193.292 °C

    Density: 1.112 g/cm3

    mg g kg ml l t