2,4-Difluoro-DL-Phenylalanine is a fluorinated, non-natural phenylalanine derivative in which two fluorine atoms are substituted at the 2- and 4-positions of the aromatic side chain, while the amino acid backbone retains an α-amino group and a carboxyl group. The molecule is provided as the DL (racemic) stereochemical form, and the side chain bears a difluorophenyl ring that can modulate aromatic electronics and hydrogen-bonding interactions relative to unsubstituted phenylalanine. As a free amino acid analogue, it is used in peptide and protein structure-function studies, chemical biology labeling strategies, and analytical method development where fluorinated aromatic residues help probe conformational effects or enable spectroscopic and mass-based detection.
CAT No: CP12703
2,4-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog supplied as a DL mixture, featuring two fluorine atoms on the aromatic ring that strongly influence electronic properties, lipophilicity, and metabolic stability trends in medicinal chemistry. As a non-natural amino acid building block, it is commonly used to probe structure-activity relationships and to introduce fluorinated aromatic motifs into peptide-like scaffolds and peptidomimetics. Its amino acid functionality enables downstream coupling into synthetic sequences, while the difluoro substitution pattern provides a chemically robust handle for SAR-driven optimization.
1. Peptidomimetic Building Blocks
2,4-Difluoro-DL-Phenylalanine is used by medicinal chemistry and chemical biology teams to incorporate a difluorinated aromatic side chain into peptidomimetic series, helping researchers evaluate how aryl fluorination affects potency trends, conformational preferences, and off-target liabilities during hit-to-lead optimization. The DL stereochemical mixture is frequently leveraged in early-stage library synthesis when rapid SAR exploration is prioritized over stereochemical purity at the analog level. In practice, the compound serves as an amino acid building block for assembling constrained or backbone-modified analogs that retain an amino acid-derived pharmacophore while varying the aryl electronics through the 2,4-difluoro pattern.
2. Structure-Activity Relationship Studies
2,4-Difluoro-DL-Phenylalanine supports SAR workflows in which aromatic substitution is systematically varied to map the contribution of ring electronics and steric/electrostatic effects. Researchers in drug discovery commonly select fluorinated phenylalanine analogs to create matched series differing only by fluorination pattern, enabling clearer interpretation of how the 2,4-disubstitution changes physicochemical behavior and interaction profiles in binding assays and functional screens. Because the fluorines are directly attached to the aromatic ring, the compound provides a direct way to tune properties without altering the amino acid backbone framework, making it a practical reagent for comparative analog synthesis and analytical characterization.
3. Pharmaceutical Intermediate Development
2,4-Difluoro-DL-Phenylalanine is also applied as a specialized intermediate for manufacturing research quantities of fluorinated amino acid derivatives used in medicinal chemistry programs. Process development teams and custom synthesis groups use it as a defined precursor to access downstream protected forms, activated derivatives, or coupling-ready intermediates that carry the difluoro-phenyl motif into larger synthetic targets. The presence of the amino acid functional group and the chemically stable C-F bonds make the compound a convenient starting point for constructing fluorinated fragments that must survive multiple synthetic steps before final assembly into peptide-like or heteroaromatic-containing scaffolds.
4. Analytical Reference Material
2,4-Difluoro-DL-Phenylalanine is frequently employed as a reference compound in analytical method development and impurity profiling for fluorinated amino acid analogs. Analytical chemists use it to confirm identity and retention behavior in LC methods, support method qualification for fluorinated building blocks, and calibrate or validate workflows that quantify difluorinated phenylalanine-containing species in synthesis monitoring. The defined difluoro substitution pattern makes it particularly useful when distinguishing closely related aromatic amino acid analogs that differ by fluorination position or degree of substitution.
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