3,4-Dichloro-L-Phenylalanine is a naturally occurring amino acid derivative in which the phenyl side chain of L-phenylalanine is substituted with two chlorine atoms at the 3 and 4 positions, yielding a halogenated, non-proteinogenic aromatic amino acid analogue. The molecule contains a free α-amino group and a free α-carboxyl group while bearing a substituted benzyl side chain that provides increased hydrophobicity and distinct electronic character compared with unsubstituted phenylalanine, with stereochemistry specified as L. It is used as a substrate in peptide synthesis and structure-activity studies to introduce halogenated aromatic residues, and it can also serve as a defined building block for analytical method development and chemical biology experiments requiring a chemically distinct phenylalanine analogue.
CAT No: CP12401
CAS No:52794-99-7
Synonyms/Alias:52794-99-7;3,4-Dichloro-L-phenylalanine;(S)-2-Amino-3-(3,4-dichlorophenyl)propanoicacid;L-3,4-Dichlorophenylalanine;(2S)-2-amino-3-(3,4-dichlorophenyl)propanoicacid;3,4-Dichloro-phenylalanine;L-3,4-DICHLOROPHE;L-3,4-Dichlorophenlalanine;H-Phe(3,4-DiCl)-OH;H-3,4-DICHLORO-PHE-OH;SBB064177;DICHLOROPHE;PubChem11970;SCHEMBL43915;3,4-DICHLORO-PHE-OH;D-3,4-Dichlorophenylalanine;AC1MC537;3,4-DICHLORO-L-PHE-OH;CTK5A9810;L-PHE(3,4-DICL)-OH;H-PHE(3,4-CL2)-OH;MolPort-001-758-768;59331-62-3;H-L-PHE(3,4-CL2)-OH;ZINC1652104
3,4-Dichloro-L-Phenylalanine is a halogenated, proteinogenic amino acid analog featuring two chlorine substituents on the aromatic side chain of L-phenylalanine. This electron-withdrawing, sterically defined phenyl ring makes it a practical building block for structure-activity relationship studies and for preparing halogen-rich peptide or small-molecule fragments where aromatic substitution pattern is a key design variable. Researchers commonly select this stereodefined amino acid when downstream products require a specific aryl substitution motif rather than the unsubstituted phenylalanine scaffold.
1. Peptide Analog Building Blocks
3,4-Dichloro-L-Phenylalanine is used to introduce a defined 3,4-dichloro-phenylalanine motif into peptide analogs for custom peptide synthesis, including solution-phase and solid-phase workflows where amino acid side-chain identity must be retained. Medicinal chemistry and chemical biology groups use this residue to probe how halogen substitution on the aromatic side chain influences conformational preferences, local hydrophobicity, and aromatic interactions in peptide sequences. The dichloro substitution pattern is particularly valuable when comparing series of analogs that differ only by aryl electronics or sterics, enabling more controlled SAR development than using generic phenylalanine.
2. Medicinal Chemistry SAR Studies
3,4-Dichloro-L-Phenylalanine supports small-molecule and peptidomimetic intermediate development where a halogenated phenylalanine-derived fragment is required to build structure-defined libraries. Pharmaceutical intermediate teams and medicinal chemistry researchers incorporate this chiral amino acid into synthetic routes that generate aryl-rich scaffolds for lead optimization, using the 3,4-dichloro pattern as a tunable element for modulating physicochemical properties and interaction geometry. Because the amino acid provides a stereodefined backbone with a pre-installed substituted aromatic ring, it is often selected when the substitution pattern must be controlled early in the synthesis of analog series.
3. Chemical Biology Probe Precursors
3,4-Dichloro-L-Phenylalanine is frequently used as a precursor for chemical biology probes and affinity reagents that require a halogenated aromatic motif to support binding-site recognition or to tune nonspecific hydrophobic interactions during probe optimization. Researchers preparing labeled peptide fragments or probe-building intermediates use this amino acid to embed the 3,4-dichloro phenyl ring into larger constructs before installing reporting or capture functionalities in subsequent steps. This approach is especially common in workflows where the aromatic substitution pattern is expected to affect how probe scaffolds engage with protein pockets, receptors, or enzyme active sites during screening and characterization.
4. Pharmaceutical Intermediate Development
3,4-Dichloro-L-Phenylalanine is applied in the manufacture of research-grade pharmaceutical intermediates and specialty chemical building blocks that rely on a halogenated, stereodefined amino acid handle. Process and development chemists use it to access dichloro-substituted aromatic fragments that can be carried through downstream transformations to generate analog libraries for preclinical discovery chemistry. The presence of the amino acid functionality provides a convenient platform for constructing derivatives while preserving the 3,4-dichloro substitution motif that is often targeted for property tuning in medicinal chemistry programs.
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