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    874948-59-1

    Catalog No. EBD3317773

    CAS 874948-59-1

    Name S-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate

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    Basic Information

    Synonyms: S-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate

    Molecular Formula: C32H21O4P

    Molecular Weight: 500.48

    Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

    Product Description:
    S-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate, commonly known as (S)-VAPOL phosphoric acid, is a chiral Brønsted acid catalyst derived from the VAPOL (vaulted biaryl phosphoric acid) ligand scaffold. Its structure features a rigid, axially chiral 1,1'-binaphthyl core with phenyl substituents at the 3,3'-positions and a phosphoric acid group at the 2,2'-positions, which serves as the active catalytic site. This compound is a prominent member of chiral phosphoric acids (CPAs) and is extensively used as an organocatalyst in asymmetric synthesis. It facilitates a wide range of enantioselective transformations, including but not limited to, Friedel-Crafts alkylations, Pictet-Spengler reactions, transfer hydrogenations, and various cycloaddition reactions. Its primary application lies in constructing chiral centers for pharmaceuticals and advanced organic materials by activating substrates through hydrogen-bonding or ion-pairing interactions. As a specialized, high-value chiral auxiliary, it is not a general-purpose synthetic building block but a dedicated catalyst precursor. Its development and use are pivotal in academic research and industrial process development for enantioselective catalysis, contributing significantly to the synthesis of optically active compounds.
    Physical Properties
    mg g kg ml l t