2,3-Dichloro-DL-Phenylalanine is a halogenated, non-natural phenylalanine derivative bearing a benzyl side chain substituted with two chlorine atoms at the 2- and 3-positions relative to the ring, and it 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 molecule retains the free amino and free carboxyl functionality without additional protecting groups, which can influence polarity, hydrogen-bonding, and reactivity in coupling chemistry. This chlorinated amino acid is used in peptide and amino acid derivative synthesis and in chemical biology or analytical studies where halogen substitution provides a handle for structural probing, method development, or incorporation of a modified aromatic residue into defined peptide structures.
CAT No: CP12003
2,3-Dichloro-DL-Phenylalanine is a halogenated phenylalanine analog featuring two chlorine substituents on the aromatic ring, supplied as a DL (racemic) mixture for synthetic and medicinal chemistry workflows. As a non-proteinogenic amino acid derivative, it is commonly used as a chemically defined building block for preparing halogenated amino acid motifs, peptidomimetic structures, and aromatic substitution patterns that influence physicochemical properties and downstream reactivity. Its amino acid functionality enables incorporation into peptide-like scaffolds and intermediate sequences where aromatic chlorination is required for structure-activity relationship studies or chemical probe generation.
1. Peptidomimetic Building Blocks
2,3-Dichloro-DL-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to construct peptidomimetic and peptide-like analogs bearing a halogenated aromatic side chain. The DL stereochemical mixture supports library and SAR workflows where multiple analogs are screened without committing to a single enantiomer at the early design stage. In practice, it serves as a defined amino acid building block for assembling substituted aromatic motifs that can be carried through to final lead candidates or reference compounds, including constrained or sterically tuned backbones where aromatic substitution is a key design variable.
2. Pharmaceutical Intermediate Synthesis
2,3-Dichloro-DL-Phenylalanine is frequently selected as a pharmaceutical intermediate precursor for manufacturing halogenated amino acid derivatives and related small-molecule fragments. Process and development chemists use it to introduce the 2,3-dichloro-phenyl substitution pattern into downstream heterocycles, aromatic side chains, or protected amino acid intermediates used in route development. The presence of both the amino acid functionality and the activated aromatic chlorination pattern makes it a practical starting material for generating chemically consistent intermediates used in parallel synthesis, scale-up planning, and comparative chemistry programs.
3. Structure-Activity Relationship Studies
2,3-Dichloro-DL-Phenylalanine supports SAR investigations where halogen substitution on the phenyl ring is used to modulate electronic character, steric environment, and chemical stability of amino acid-derived scaffolds. Research teams in chemical biology and medicinal chemistry incorporate this building block into series of analogs to isolate the impact of aromatic chlorination while keeping the amino acid core constant. The defined dichloro substitution pattern enables straightforward comparison against mono-halogenated or non-halogenated analogs, helping teams map how aromatic substitution correlates with observed properties in assay panels and lead optimization campaigns.
4. Analytical Reference Compound Development
2,3-Dichloro-DL-Phenylalanine is also used as a reference material for analytical method development and characterization of halogenated amino acid derivatives. Analytical chemistry laboratories employ it to support LC method scouting, impurity profiling, and identification of amino acid-derived components in synthetic mixtures and intermediate streams. Because the compound is a discrete, structurally defined aromatic dichloro amino acid, it is commonly leveraged when developing workflows that require reliable standards for retention-time assignment, mass-based confirmation, and compositional verification of related chlorinated analogs.
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