3-Fluoro-DL-Phenylalanine

3-Fluoro-DL-Phenylalanine is a fluorinated, non-natural phenylalanine derivative in which a fluorine substituent is positioned at the 3-position of the aromatic side chain, yielding a DL stereochemical mixture at the alpha carbon. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, while the aromatic ring bears the fluorine atom that can modulate electronic properties and influence hydrophobic and hydrogen-bonding interactions through the C-F bond. As a structurally defined building block, it is used in peptide and amino acid derivative synthesis and in structure-activity or labeling studies where incorporation of a fluorinated phenylalanine analogue enables analytical differentiation and side-chain property tuning.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP14503

CAS No:456-88-2

Synonyms/Alias:3-Fluoro-dl-phenylalanine;3-Fluorophenylalanine;2-amino-3-(3-fluorophenyl)propanoicacid;m-Fluorophenylalanine;456-88-2;m-Fluoro-dl-phenylalanine;Alanine,(3-fluorophenyl)-;2629-54-1;3-Fluoro-3-phenylalanine;Phenylalanine,3-fluoro-;ALANINE,3-(m-FLUOROPHENYL)-;NSC208960;m-Fluorophenylalanine(VAN);dl-beta-m-Fluorophenylalanine;2-Amino-3-(3-fluorophenyl)propionicAcid;H-DL-PHE(3-F)-OH;DL-3-Fluorophenylalanine;DL-3-(3-Fluorophenyl)alanine;VWHRYODZTDMVSS-UHFFFAOYSA-N;EINECS207-272-1;ST024949;qvyz1rcf&&dlform;ACMC-20a6cq;dl-m-Fluorophenylalanine;ACMC-1BVWR

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M.F/Formula
C9H10FNO2
M.W/Mr.
183.18

3-Fluoro-DL-Phenylalanine is a fluorinated phenylalanine analog supplied as a DL mixture, combining both D- and L-stereochemical forms with a ring fluorine substituent that strongly influences aromatic electronics and metabolic stability trends in chemical biology workflows. As an amino acid building block, it provides a direct handle for incorporating fluorinated aromatic chemistry into peptide-like structures and medicinal chemistry intermediates where controlled stereochemical composition and fluorine-driven physicochemical effects are required. Researchers also use it as a defined fluorinated amino acid reference material for method development in LC-MS based studies.

1. Peptidomimetic Building Block

3-Fluoro-DL-Phenylalanine is used by medicinal chemistry and chemical biology groups to construct peptidomimetic scaffolds and fluorinated amino acid-containing analogs for structure-activity relationship studies. The fluorine-substituted phenyl side chain offers a practical way to introduce a single electronegative substituent into an otherwise phenylalanine-like motif, enabling downstream evaluation of how aromatic fluorination affects chemical behavior in synthetic and assay contexts. Because the material is supplied as a DL mixture, it is frequently selected for early-stage library synthesis and comparative studies where stereochemical separation is not yet required.

2. Medicinal Chemistry Intermediate

3-Fluoro-DL-Phenylalanine serves as a fluorinated amino acid intermediate for synthesis of non-natural amino acid derivatives used in small-molecule and peptide-drug discovery programs. In these workflows, the presence of a fluorinated aromatic ring provides a stable, chemically addressable modification that can be carried through to final analogs, including protected amino acid derivatives and coupling-ready formats prepared by downstream processing. The DL composition is often advantageous for exploratory intermediate development, where rapid access to fluorinated scaffolds is prioritized before any later stereochemical refinement.

3. LC-MS Analytical Standard

3-Fluoro-DL-Phenylalanine is commonly employed as a defined fluorinated amino acid standard for analytical method development and calibration in LC-MS workflows. Analytical chemists use it to verify retention behavior and mass-based detection of fluorinated phenylalanine analogs in complex matrices, such as reaction mixtures, metabolite screening extracts, or synthetic intermediate panels. The DL mixture also supports robust method qualification when the analytical goal is to track the presence of the compound class rather than to resolve D/L stereoisomers at the earliest development stage.

Abbr
DL-3-F-Phe-OH
InChI
1S/C9H10FNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
InChI Key
VWHRYODZTDMVSS-UHFFFAOYSA-N
Canonical SMILES
C1=CC(=CC(=C1)F)CC(C(=O)O)N

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