2,6-Dichloro-DL-Phenylalanine is a halogenated phenylalanine derivative in which the phenyl side chain bears two chlorine substituents at the 2- and 6-positions, and the molecule contains both an amino group and a carboxyl group characteristic of amino acid frameworks. The "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon, and the side chain functionality is dominated by the dichloro-substituted aromatic ring rather than the native phenylalanine ring electronics, while the amino and carboxyl groups support standard amino acid salt formation and coupling chemistry. This compound is used in peptide and amino acid derivative synthesis and in structure-property studies where aryl halogenation can modulate hydrophobicity, steric profile, and spectroscopic or analytical behavior for labeling, conjugation, or chemical biology workflows.
CAT No: CP12303
2,6-Dichloro-DL-Phenylalanine is a halogenated phenylalanine analog supplied as a DL mixture, featuring two chlorine substituents at the 2- and 6-positions of the aromatic ring. This substitution pattern increases steric bulk and alters electronic properties relative to unsubstituted phenylalanine, making it a practical building block for preparing halogenated amino-acid motifs in peptide and medicinal chemistry programs. Researchers commonly select this compound when they need a defined chlorinated aromatic side chain for structure-activity relationship studies, protease/peptidomimetic stability evaluations, or as a chemically robust intermediate for further functionalization.
1. Peptidomimetic Building Block
2,6-Dichloro-DL-Phenylalanine is used as a non-natural amino acid building block for constructing peptidomimetics and modified peptide analogs where a chlorinated, sterically hindered aromatic side chain is required. Medicinal chemistry groups incorporate this motif into short peptide leads, constrained analogs, and SAR libraries to probe how aryl substitution patterning influences conformational preferences and overall physicochemical behavior. Because the compound is supplied as a DL mixture, it is often chosen for parallel library synthesis where relative stereochemical effects are evaluated empirically rather than controlled at the single-enantiomer level.
2. Medicinal Chemistry SAR Studies
2,6-Dichloro-DL-Phenylalanine supports medicinal chemistry workflows focused on aromatic halogen effects, including tuning lipophilicity, electronic distribution, and steric shielding around the phenyl ring. Small-molecule and peptide-drug discovery teams use this amino acid analog to generate chlorinated analog series that can be carried forward into downstream hit-to-lead optimization and structure-activity relationship mapping. The dichloro substitution pattern is particularly useful when researchers want a defined, reproducible aromatic handle that can be retained through subsequent synthetic steps and incorporated into larger scaffolds as an amino-acid-derived fragment.
3. Pharmaceutical Intermediate Synthesis
2,6-Dichloro-DL-Phenylalanine is also employed as a pharmaceutical intermediate for producing chlorinated aromatic amino-acid derivatives and related building blocks used in custom synthesis. Process and development chemists rely on this starting material to access downstream intermediates that maintain the 2,6-dichloro phenyl motif while allowing variation at the amino and carboxyl functionalities during derivative elaboration. This makes the compound a practical choice for industrial and contract synthesis settings that require a stable, well-defined halogenated amino-acid precursor for assembling more complex structures, including protected amino-acid derivatives and functionalized intermediates for further coupling chemistry.
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