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    261360-77-4

    Catalog No. EBD13478

    CAS 261360-77-4

    Name Boc-3-bromo-D-phenylalanine

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    Basic Information

    Synonyms: Boc-3-bromo-D-phenylalanine (R)-N-BOC-3-Bromophenylalanine Boc-D-3-Bromophenylalanine n-tert-butoxycarbonyl-3-bromophenyl-d-alanine

    Molecular Formula: C14H18BrNO4

    Molecular Weight: 344.2

    MDL Number: MFCD01317704

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Amines

    Product Description:
    Boc-3-bromo-D-phenylalanine is a chiral, non-natural amino acid derivative. Its chemical structure features a D-phenylalanine core substituted with a bromine atom at the meta-position of the phenyl ring and protected at the N-terminus with a tert-butyloxycarbonyl (Boc) group. This specific combination of a halogenated aromatic side chain and a protected amine makes it a valuable, specialized building block. This compound is primarily employed as a key intermediate in the synthesis of peptide-based pharmaceuticals and bioactive molecules. The presence of the bromine atom on the aromatic ring provides a versatile handle for further functionalization via cross-coupling reactions (e.g., Suzuki, Heck), allowing for the introduction of diverse substituents to fine-tune the properties of the final drug candidate. The Boc protecting group is crucial for standard solid-phase peptide synthesis (SPPS) protocols, enabling selective deprotection and chain elongation. Its main application lies in medicinal chemistry research and the development of novel therapeutic agents, particularly where the incorporation of a modified phenylalanine residue is required to modulate activity, selectivity, or metabolic stability. As a protected, halogenated D-amino acid, it serves as a critical chiral synthon for constructing complex peptide architectures.
    Physical Properties

    Boiling Point: 475.3 °C at 760 mmHg

    Flash Point: 241.2 °C

    Density: 1.405 g/cm3

    Storage: Store at 0°C

    Analytical Data

    Appearance: off-white crystalline powder

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