2-Chloro-DL-Phenylalanine is a halogenated, non-proteinogenic amino acid derivative featuring a benzyl side chain bearing a chloro substituent at the 2-position relative to the aromatic ring and a free amino group and carboxyl group on the α-carbon. The "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon, and the molecule retains the phenylalanine backbone while introducing a chloro functionality that alters polarity and provides a chemically distinct aromatic handle for further derivatization. In peptide and chemical biology workflows, this compound is used as a substrate analog or building block to generate modified peptides and to support structure-activity studies, labeling strategies, or analytical method development where a phenylalanine-like residue with a halogenated aromatic side chain is required.
CAT No: CP11403
CAS No:14091-11-3
Synonyms/Alias:2-Chloro-DL-Phenylalanine;2-amino-3-(2-chlorophenyl)propanoicacid;14091-11-3;2-chlorophenylalanine;o-Chloro-dl-phenylalanine;DL-PHE(2-CL)-OH;2-Amino-3-(2-chloro-phenyl)-propionicacid;DL-Phenylalanine,2-chloro-;NSC28185;O-Chlorophenylalanine;ACMC-20anxv;ACMC-209piz;AC1Q3PEU;2-Chloro-D-Phe-OH.HCl;SCHEMBL43976;DL-O-CHLOROPHENYLALANINE;2-Chloro-3-phenyl-DL-alanine;AC1L39Z5;DL-beta-(o-Chlorophenyl)alanine;CTK8B5709;MolPort-003-894-416;EINECS237-939-2;ANW-49743;AR-1E0757;MFCD00037774
2-Chloro-DL-Phenylalanine is a halogenated phenylalanine derivative supplied as a racemic DL mixture, providing both D- and L- stereoisomers for synthetic and analytical workflows. The side chain retains the phenylalanine aromatic character while the alpha- and/or ring-substituted chloro functionality enables downstream derivatization and incorporation into halogenated analog libraries. This compound is commonly handled as a research-grade amino acid building block for structure-driven chemistry, including medicinal chemistry intermediate development and stereochemical method development where access to both enantiomers is advantageous.
1. Peptidomimetic Building Blocks
2-Chloro-DL-Phenylalanine is used as an amino acid building block in the preparation of halogenated peptidomimetics and peptide analogs for structure-activity relationship studies. Medicinal chemistry teams and peptide chemistry laboratories often select this type of chlorinated phenylalanine to introduce a defined steric/electronic perturbation on the aromatic side-chain environment while maintaining the amino acid framework required for coupling into protected peptide segments. Because the material is supplied as a DL mixture, it is frequently chosen for early-stage library synthesis and for workflows where both enantiomeric forms are processed in parallel prior to enantiopure optimization.
2. Pharmaceutical Intermediate Development
2-Chloro-DL-Phenylalanine serves as a practical intermediate for industrial and contract synthesis programs that require chlorinated amino acid motifs as precursors to further functionalized derivatives. Chemical development groups use such halogenated amino acid starting materials to access downstream intermediates bearing reactive handles for substitution, coupling, or elaboration into more complex heterocycles and substituted aromatic frameworks. The presence of the chloro substituent supports synthetic diversification strategies, making the compound useful when route scouting or analog generation requires a readily available, amino-acid-derived scaffold rather than starting from simpler chlorinated aromatics.
3. Stereochemical Method Development
2-Chloro-DL-Phenylalanine is frequently employed in analytical and process development contexts where racemic amino acid substrates are needed to evaluate chiral separation performance or to benchmark derivatization and quantification workflows. Laboratories developing chiral HPLC methods, chiral derivatization strategies, or enantiomer-resolved LC-MS assays often use DL amino acids to confirm baseline behavior and to generate calibration material for enantiomer ratio determination. The availability of both D- and L- forms in one reagent also supports method robustness studies during process optimization and quality-by-design investigations for chirality-critical intermediates.
4. Halogenated Analog Libraries
2-Chloro-DL-Phenylalanine is applied in the synthesis of halogenated analog panels used for chemical biology screening and SAR exploration, where controlled incorporation of a chloro-substituted phenylalanine motif can be used to probe structure-property relationships. Research groups building small-molecule or peptide-based libraries rely on amino acid-derived scaffolds to standardize coupling chemistry across analogs while varying substituents at the aromatic position. Supplying the compound as a DL mixture accelerates library generation when enantiomer-specific effects are not yet the primary variable, enabling faster iteration toward enantiopure candidates in later optimization stages.
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