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    106268-96-6

    Catalog No. EBD14279

    CAS 106268-96-6

    Name (2R)-(-)-2-METHYLGLYCIDYL 4-NITROBENZOATE

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    Basic Information

    Synonyms: (2r)-(-)-(2,3-epoxy-2-methylpropylester)-4-nitrobenzoate 3-methyl-,4-nitrobenzoate,(r)-oxiranemethano 2,3-EPOXY-2-METHYLPROPYLESTER-4-NITROBENZOATE 2-methylglycidyl4-nitrobenzoate [(2R)-3-methyloxiran-2-yl]methyl4-nitrobenzoate (2R)-(-)-2-METHYLGLYCIDYL4-NITROBENZOATE

    Molecular Formula: C11H11NO5

    Molecular Weight: 237.21

    MDL Number: MFCD00012315

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

    Product Description:
    (2R)-(−)-2-Methylglycidyl 4-nitrobenzoate is a chiral epoxide derivative, specifically an enantiomerically pure compound with the (R)-configuration. It is characterized by the presence of a methyl-substituted oxirane (epoxide) ring esterified with 4-nitrobenzoic acid. This structure makes it a valuable chiral building block in asymmetric synthesis. Its primary and most significant application is as a key chiral intermediate in the pharmaceutical industry. It is notably used in the synthesis of β-blocker drugs, such as (S)-propranolol and other related adrenergic antagonists. The chiral epoxide ring serves as a reactive handle for nucleophilic ring-opening reactions with amines or other nucleophiles, allowing for the stereoselective construction of the drug's active enantiomer. The 4-nitrobenzoate group acts as a good leaving group, facilitating these transformations. As a high-value chiral synthon, it is employed in research and development for constructing molecules with defined stereocenters. Its utility extends beyond specific drug syntheses to general methodologies in organic chemistry that require enantiopure epoxide precursors. Handling requires standard precautions for reactive organic compounds.
    Physical Properties

    Melting Point: 87-89 °C(lit.)

    Boiling Point: 382.6°C at 760 mmHg

    Flash Point: 178.3°C

    Density: 1.321g/cm3

    Storage: 2-8°C

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