2,4-Dichloro-L-Phenylalanine is a halogenated, proteinogenic amino acid derivative in which the phenylalanine aromatic ring bears two chlorine substituents at the 2 and 4 positions. The molecule contains an α-amino group and a carboxyl group with an L-stereochemical configuration, while the side chain is a substituted benzyl group that introduces increased hydrophobicity and potential sites for electrophilic and aromatic interactions. As a chemically modified phenylalanine analogue, it is used in peptide synthesis and structure-activity or structure-property studies to probe the effects of ring halogenation on peptide conformation, binding interactions, and analytical behavior.
CAT No: CP12101
CAS No:111119-36-9
Synonyms/Alias:111119-36-9;2,4-Dichloro-L-phenylalanine;L-2,4-Dichlorophenylalanine;(S)-2-Amino-3-(2,4-dichlorophenyl)propanoicacid;(2S)-2-amino-3-(2,4-dichlorophenyl)propanoicacid;L-2,4-DICHLOROPHE;2,4-DICHLORO-PHENYLALANINE;SBB064546;(S)-2-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONICACID;PubChem18710;2,4-dichlorophenylalanine;(2R)-2-Amino-3-(2,4-dichlorophenyl)propionicacid;SCHEMBL44905;AC1MC534;CTK7I3496;H-PHE(2,4-DICL)-OH;L-PHE(2,4-DICL)-OH;GWHQTNKPTXDNRM-QMMMGPOBSA-N;H-PHE(2,4-CL2)-OH;MolPort-001-758-766;H-L-PHE(2,4-CL2)-OH;ZINC1652105;CD-705;AB10100;AC-5846
2,4-Dichloro-L-Phenylalanine is a halogenated phenylalanine building block featuring two chlorine substituents on the aromatic ring and the L-configuration at the alpha-carbon. This non-proteinogenic aromatic amino acid is commonly used in peptide and peptidomimetic synthesis to introduce a defined hydrophobic and electron-withdrawing side-chain environment, supporting structure-property studies and medicinal chemistry lead optimization. Its aryl dichloro pattern also makes it a practical intermediate for downstream functionalization strategies where controlled aromatic substitution is required.
1. Peptidomimetic Building Blocks
2,4-Dichloro-L-Phenylalanine is used by peptide chemistry groups to incorporate a halogenated aromatic residue into custom peptides and peptidomimetics for SAR (structure-activity relationship) and conformational/physicochemical tuning. The dichloro-substituted phenyl side chain provides a distinct steric and electronic profile compared with standard phenylalanine, which is valuable when researchers need to probe how aromatic substitution affects binding-site interactions, local hydrophobicity, and overall peptide behavior. In practice, it is selected as a defined amino acid component during the assembly of analog series where consistent side-chain substitution is critical for interpreting structure-property trends.
2. Medicinal Chemistry SAR Studies
2,4-Dichloro-L-Phenylalanine supports medicinal chemistry workflows focused on designing and comparing analogs that contain halogenated aromatic motifs. Medicinal chemistry teams frequently use halogenated amino acid residues to modulate lipophilicity and electronic character within peptide-like scaffolds, improving the interpretability of SAR campaigns without changing the backbone framework. Because the aromatic substitution pattern is fixed at the amino acid stage, the compound helps ensure that each analog in a library carries the same dichloro-phenyl motif, enabling more reliable comparisons across synthesis batches and downstream biological or biophysical characterization programs.
3. Pharmaceutical Intermediate Development
2,4-Dichloro-L-Phenylalanine is also used as a research-grade intermediate for preparing substituted aromatic derivatives relevant to pharmaceutical and specialty chemical development. The presence of two chlorine atoms on the phenyl ring provides handles for further derivatization routes commonly pursued in medicinal chemistry, such as selective aromatic transformations that preserve the amino acid stereochemical integrity. Process development and intermediate synthesis teams value this building block when they need a well-defined, stereochemically consistent starting material that already contains the targeted dichloro substitution pattern for later diversification steps.
4. Chemical Biology Probe Analogues
2,4-Dichloro-L-Phenylalanine is employed in chemical biology and probe-development programs where peptide-like recognition elements are modified with halogenated aromatic residues to tune interaction properties of probe scaffolds. Researchers often incorporate this amino acid into probe analogues to create defined aromatic environments that can influence how a probe scaffold engages a binding pocket or recognizes a molecular surface in assay systems. By using a fixed dichloro-phenylalanine residue, teams can generate probe series with controlled side-chain substitution, which is particularly useful when comparing probe analogs that differ only in aromatic electronics or hydrophobic character.
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