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    58520-04-0

    Catalog No. EBD39791

    CAS 58520-04-0

    Name 1R,2R-1,2-Di(4'-methoxyphenyl)-1,2-diaminoethan

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    Basic Information

    Synonyms: 1R,2R-1,2-Di(4'-methoxyphenyl)-1,2-diaminoethan (1R,2R)-1,2-Di(4'-methoxyphenyl)-1,2-diaminoethane (S,S)-DAEN

    Molecular Formula: C16H20N2O2

    Molecular Weight: 272.34

    MDL Number: MFCD08460192

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

    Product Description:
    (1R,2R)-(-)-1,2-Bis(4-methoxyphenyl)ethylenediamine is a chiral diamine compound characterized by its (1R,2R) absolute configuration. It is a white to off-white crystalline powder with a molecular formula of C₁₆H₂₀N₂O₂. This compound is a derivative of 1,2-diphenylethylenediamine (DPEN) with methoxy substituents on the phenyl rings. Its primary and most significant application is as a chiral ligand and building block in asymmetric synthesis, particularly in the pharmaceutical industry. It is a key precursor for the synthesis of highly effective chiral catalysts, such as the Noyori-Ikariya type ruthenium complexes (e.g., [(R,R)-TsDPEN RuCl(p-cymene)]). These catalysts are renowned for the asymmetric transfer hydrogenation (ATH) of prochiral ketones to produce enantiomerically pure secondary alcohols, a critical transformation in the manufacture of many active pharmaceutical ingredients (APIs). The methoxy groups can enhance the ligand's electronic properties and solubility. Due to its crucial role in producing enantioselective catalysts for drug synthesis, it is fundamentally classified as a pharmaceutical intermediate. Its direct and specialized use as a ligand component also justifies its classification within the catalyst and ligand category of synthetic chemistry.
    Physical Properties

    Melting Point: 89-91°C

    Boiling Point: 438.2°Cat760mmHg

    Flash Point: 231.9°C

    Density: 1.135g/cm3

    mg g kg ml l t