Description

(S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid (CAS No. 130855-57-1) is a high-purity fluorinated amino acid derivative with the molecular formula C₁₀H₁₂FNO₂. This chiral compound, also known as alpha-methyl-L-4-Fluorophenylalanine, features a stereospecific (S)-configuration and a methyl substitution at the alpha-position, making it a valuable building block for peptidomimetics and pharmaceutical research. The 4-fluorophenyl moiety enhances metabolic stability and bioavailability in drug design applications. Supplied as a white to off-white crystalline powder, this reagent is characterized by HPLC purity ≥95% and is rigorously tested for heavy metals, residual solvents, and chiral purity. Ideal for medicinal chemistry, it is packaged under inert gas in amber glass vials to ensure long-term stability. Store at 2-8°C in a dry environment.

Properties

• CAS Number: 130855-57-1
• Complexity: 214
• IUPAC Name: (2S)-2-amino-3-(4-fluorophenyl)-2-methyl-propanoic acid
• InChI: InChI=1S/C10H12FNO2/c1-10(12,9(13)14)6-7-2-4-8(11)5-3-7/h2-5H,6,12H2,1H3,(H,13,14)/t10-/m0/s1
• InChI Key: BBRMBENCQBOTHY-JTQLQIEISA-N
• Exact Mass: 197.08520679
• Molecular Formula: C10H12FNO2
• Molecular Weight: 197.21
• SMILES: C[C@](CC1=CC=C(C=C1)F)(C(=O)O)N
• Topological: 63.3
• Monoisotopic Mass: 197.08520679
• Synonyms: 130855-57-1, (S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid, alpha-methyl-L-4-Fluorophenylalanine, (2S)-2-AMINO-3-(4-FLUOROPHENYL)-2-METHYLPROPANOIC ACID, L-Phenylalanine, 4-fluoro-alpha-methyl-, H-4-fluoro-alpha-Me-Phe-OH, alpha-methyl-D-4-Fluorophe, 4-Fluoro-alpha-methyl-L-phenylalanine, H-4-fluoro–Me-Phe-OH, SCHEMBL1817058, DTXSID60469114, 4-Fluoro-a-methyl-L-phenylalanine, MFCD08061612, (S)-alpha-Methyl-4-fluorophenylalaine, AKOS016843481, AB43348, PS-12887, DB-328081, CS-0444272, G84964, (S)-2-AMINO-3-(4-FLUOROPHENYL)-2-METHYLPROPANOICACID, (R)-alpha-Methyl-4-fluorophenylalanine, (R)-2-Amino-2-methyl-3-(4′-fluorophenyl)propanoic acid (H-D-aMePhe(4-F)-OH)

Application

This fluorinated non-natural amino acid is widely used as a key intermediate in the synthesis of protease inhibitors and kinase-targeted therapeutics. Its structural rigidity and enhanced lipophilicity make it valuable for improving peptide stability and membrane permeability in drug candidates. Researchers employ it in structure-activity relationship (SAR) studies for CNS drugs due to its ability to cross the blood-brain barrier. The compound is also utilized in PET tracer development, leveraging the fluorine-19 atom for potential ¹⁸F radiolabeling applications.

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