3,4-Dichloro-DL-Phenylalanine is a halogenated, non-proteinogenic phenylalanine derivative bearing two chlorine substituents on the aromatic ring at the 3- and 4-positions, with the amino acid backbone retaining both an amino group and a carboxyl group. The "DL" designation indicates a racemic mixture of stereoisomers at the alpha carbon, and the side chain features a dichlorophenyl moiety that alters hydrophobicity and electronic character relative to unsubstituted phenylalanine while remaining suitable for incorporation as an amino acid building block. In peptide and chemical biology workflows, this dichloro-substituted amino acid is used in structure-activity studies, analog synthesis, and labeling or conjugation strategies where aryl halogen substitution provides a defined handle for downstream derivatization or comparative SAR design.
CAT No: CP12403
CAS No:5472-67-3
Synonyms/Alias:2-amino-3-(3,4-dichlorophenyl)propanoicacid;5472-67-3;3,4-dichlorophenylalanine;3,4-Dichloro-DL-Phenylalanine;NSC14789;AC1Q3O8N;SCHEMBL43914;AC1L5E18;CTK8B8263;MolPort-003-990-085;59331-62-3;NSC29444;H-DL-PHE(3,4-CL2)-OH;7949AB;ANW-59818;AR-1E9133;CD-738;DL-3,4-DICHLOROPHENYLALANINE;NSC-14789;NSC-29444;AKOS000187544;AKOS016843265;AB33552;AM82042;PS-3749
3,4-Dichloro-DL-Phenylalanine is a halogenated phenylalanine derivative supplied as a racemic (DL) mixture, featuring two chloro substituents on the aromatic ring that strongly influence sterics and electronics while preserving the amino acid backbone for downstream derivatization. This compound is commonly handled as a synthetic amino acid building block for medicinal chemistry and peptidomimetic design, where aryl dichloro substitution is used to tune physicochemical properties and provide a robust aromatic motif for further functionalization.
1. Peptidomimetic Building Block
3,4-Dichloro-DL-Phenylalanine is used as an amino acid building block in peptidomimetic and structure-activity relationship (SAR) studies, particularly when researchers need a phenylalanine-like residue bearing electron-withdrawing aryl dichloro substitution. Medicinal chemistry groups incorporate this motif into short peptide analogs and constrained scaffolds to probe how aromatic halogenation affects binding-site shape complementarity and overall molecular properties. Because the compound retains the amino acid functionality, it is also a practical starting point for preparing protected derivatives that can be carried through peptide-like assembly workflows.
2. Pharmaceutical Intermediate Development
3,4-Dichloro-DL-Phenylalanine serves as a versatile intermediate for the synthesis of halogenated aromatic amine and amino acid-derived fragments used in pharmaceutical intermediate pipelines. Process and development chemists value the dichlorinated ring as a stable, readily transformed aromatic handle for subsequent derivatization steps that lead to substituted anilines, aromatic heterocycles, or aryl-containing side chains. The DL stereochemical form is frequently acceptable at the stage where the intermediate is further elaborated into downstream structures that will later be optimized for stereochemistry or separated as needed.
3. Chiral Resolution Research
3,4-Dichloro-DL-Phenylalanine is frequently selected for chiral chemistry workflows where racemic amino acid starting materials are used to generate enantiopure derivatives. Research groups exploring stereochemical effects in amino acid-derived scaffolds may use this DL material as the feedstock for resolution strategies, enabling access to single-enantiomer analogs for subsequent SAR campaigns or receptor/target interaction studies. The presence of the 3,4-dichloro aromatic substitution provides a distinct stereochemical environment that can be advantageous when screening resolution conditions and downstream derivative formation.
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