2,4-Dichloro-DL-Phenylalanine is a halogenated, non-natural phenylalanine derivative in which the phenyl side chain bears two chlorine substituents at the 2- and 4-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 chlorinated aromatic side chain provides increased hydrophobicity and altered electronic character compared with unmodified phenylalanine while retaining the amino acid connectivity for peptide-related chemistry. As a substituted amino acid building block, it is used in peptide synthesis and structure-activity or structure-property studies to introduce halogenated aromatic residues for studying effects of side-chain halogenation on conformation, binding interactions, and analytical behavior.
CAT No: CP12103
2,4-Dichloro-DL-Phenylalanine is a chlorinated phenylalanine derivative supplied as a DL (racemic) mixture, featuring two chlorine substituents on the aromatic ring that strongly influence sterics and electronic properties. This non-proteinogenic amino acid building block is typically used to introduce halogenated aromatic functionality into peptide-like structures and medicinal chemistry scaffolds, where the dichloro substitution pattern can support structure-property studies and downstream synthetic diversification. Due to its amino acid functionality, it is commonly handled as a chemical intermediate for incorporation into larger molecules rather than as a native protein-forming residue.
1. Medicinal Chemistry Building Block
2,4-Dichloro-DL-Phenylalanine is used by medicinal chemistry groups to prepare halogenated analogs for structure-activity relationship (SAR) and structure-property optimization. The 2,4-dichloro-substituted phenyl ring provides a distinct electronic and steric profile compared with unsubstituted phenylalanine, making it valuable when researchers need to probe how aromatic halogenation affects binding-site interactions, conformational preferences, or physicochemical behavior in lead series. In practical workflows, it is incorporated into non-natural amino acid derivatives, peptidomimetic fragments, and intermediate scaffolds that later feed into library synthesis and analog generation.
2. Peptidomimetic And Analog Synthesis
2,4-Dichloro-DL-Phenylalanine supports the synthesis of peptide-like molecules and peptidomimetics where a halogenated aromatic side chain is required for chemical diversity. Research teams developing constrained or modified backbones often select this building block to install the dichloroaryl motif at a defined position, enabling consistent comparison across analog sets. Because the material is supplied as a DL mixture, it is frequently chosen for early-stage chemistry and library construction where racemic incorporation is acceptable for downstream screening, assay development, or further stereochemical refinement.
3. Pharmaceutical Intermediate Development
2,4-Dichloro-DL-Phenylalanine is routinely used as a pharmaceutical intermediate to access chlorinated aromatic fragments for broader small-molecule synthesis. Industrial and contract manufacturing chemistries value amino acid-derived intermediates when a protected or functionalized amino acid platform is needed to build larger targets with controlled functional group placement. The dichloro substitution pattern can also be advantageous for subsequent derivatization steps, including transformations that rely on the stability of the chlorinated aromatic ring while other portions of the molecule are modified to reach the desired final scaffold.
4. Chemical Biology Probe And Tagging Precursors
2,4-Dichloro-DL-Phenylalanine is employed as a precursor building block in chemical biology programs that require halogenated aromatic handles for labeling strategies or probe scaffold diversification. Teams designing affinity reagents, tool compounds, or analytical tags often incorporate halogenated amino acid motifs to tune hydrophobicity, aromatic interactions, or reactivity of the overall probe architecture. In these workflows, the amino acid functionality enables attachment to larger constructs, while the 2,4-dichloroaryl pattern provides a chemically robust aromatic element that can be carried through multi-step probe assembly.
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