Cas no 266360-61-6 (2,5-Difluoro-D-Phenylalanine)

2,5-Difluoro-D-Phenylalanine is a fluorinated derivative of the non-natural amino acid D-phenylalanine, characterized by the substitution of hydrogen atoms with fluorine at the 2 and 5 positions of the phenyl ring. This modification enhances its metabolic stability and resistance to enzymatic degradation, making it valuable in medicinal chemistry and peptide research. The fluorine atoms introduce steric and electronic effects that can influence binding affinity and selectivity in bioactive compounds. Its chiral purity (D-configuration) further supports its use in the design of enantioselective inhibitors or probes. The compound is particularly useful in PET imaging and drug development due to its potential for improved pharmacokinetic properties.
2,5-Difluoro-D-Phenylalanine structure
2,5-Difluoro-D-Phenylalanine structure
Product Name:2,5-Difluoro-D-Phenylalanine
CAS No:266360-61-6
MF:C9H9F2NO2
MW:201.1700694561
MDL:MFCD07371999
CID:67348
PubChem ID:716293
Update Time:2025-11-02

2,5-Difluoro-D-Phenylalanine Chemical and Physical Properties

Names and Identifiers

    • 2,5-Difluoro-D-Phenylalanine
    • (R)-2-Amino-3-(2,5-difluorophenyl)propanoic acid
    • (r)-2-amino-3-(2,5-difluoro-phenyl)-propionic acid
    • AC1LEQCF
    • d-2,5-difluorophenylalanine
    • H-D-PHE(2,5-F2)-OH
    • MolPort-002-501-509
    • PubChem17973
    • MFCD07371999
    • 266360-61-6
    • A818535
    • (r)-2-amino-3-(2,5-difluorophenyl)propionic acid
    • DTXSID90351992
    • CS-0170902
    • (2R)-2-amino-3-(2,5-difluorophenyl)propanoic acid
    • AS-37653
    • (R)-2-Amino-3-(2,5-difluorophenyl)propanoicacid
    • D-Phenylalanine,2,5-difluoro-
    • AKOS012010226
    • MDL: MFCD07371999
    • Inchi: 1S/C9H9F2NO2/c10-6-1-2-7(11)5(3-6)4-8(12)9(13)14/h1-3,8H,4,12H2,(H,13,14)/t8-/m1/s1
    • InChI Key: YHYQITHAFYELNW-MRVPVSSYSA-N
    • SMILES: FC1C=CC(=CC=1C[C@H](C(=O)O)N)F

Computed Properties

  • Exact Mass: 201.06017
  • Monoisotopic Mass: 201.06
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 213
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 63.3A^2
  • XLogP3: -1.2

Experimental Properties

  • Color/Form: White to Yellow Solid
  • Density: 1.379
  • Boiling Point: 304.2°Cat760mmHg
  • Flash Point: 137.8°C
  • Refractive Index: 1.536
  • PSA: 63.32
  • LogP: 1.61950

2,5-Difluoro-D-Phenylalanine Security Information

2,5-Difluoro-D-Phenylalanine Pricemore >>

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2,5-Difluoro-D-Phenylalanine Related Literature

Additional information on 2,5-Difluoro-D-Phenylalanine

Exploring the Properties and Applications of 2,5-Difluoro-D-Phenylalanine (CAS No. 266360-61-6) in Modern Research

In the realm of synthetic amino acids, 2,5-Difluoro-D-Phenylalanine (CAS No. 266360-61-6) has garnered significant attention due to its unique structural and biochemical properties. This fluorinated derivative of phenylalanine is widely utilized in pharmaceutical research, peptide synthesis, and material science. Its fluorine substitution at the 2 and 5 positions enhances metabolic stability and bioavailability, making it a valuable building block for drug discovery and development.

The growing interest in fluorinated amino acids like 2,5-Difluoro-D-Phenylalanine stems from their ability to mimic natural amino acids while offering improved resistance to enzymatic degradation. Researchers are increasingly exploring its role in designing peptide-based therapeutics, particularly in targeting protein-protein interactions and enzyme inhibition. The compound's CAS No. 266360-61-6 is frequently searched in academic databases, reflecting its relevance in cutting-edge studies.

One of the most discussed applications of 2,5-Difluoro-D-Phenylalanine is in the development of PET (Positron Emission Tomography) tracers. The incorporation of fluorine atoms allows for radiolabeling with fluorine-18, enabling non-invasive imaging of biological processes. This aligns with the current trend of precision medicine and theranostics, where molecular imaging plays a pivotal role in diagnostics and treatment monitoring.

Another area of interest is the compound's potential in bioconjugation and drug delivery systems. Its aromatic ring and fluorine atoms provide sites for selective modifications, facilitating the creation of targeted therapies. Recent studies have highlighted its utility in antibody-drug conjugates (ADCs), a rapidly advancing field in oncology and autoimmune disease treatment.

From a synthetic chemistry perspective, 2,5-Difluoro-D-Phenylalanine presents challenges and opportunities in asymmetric synthesis and chiral resolution. The demand for enantiomerically pure compounds in pharmaceuticals has driven innovations in its production methods, including enzymatic resolution and transition metal-catalyzed reactions. These advancements are often discussed in forums focusing on green chemistry and sustainable synthesis.

In material science, the compound's fluorine-rich structure contributes to the development of bioinspired materials with enhanced thermal and chemical stability. Its incorporation into polymers and coatings is being explored for applications in biomedical devices and tissue engineering, addressing the need for durable and biocompatible materials.

As the scientific community continues to investigate 2,5-Difluoro-D-Phenylalanine, its versatility across disciplines underscores its importance. Whether in drug design, molecular imaging, or advanced materials, this compound exemplifies the intersection of chemistry and biology in addressing contemporary challenges. With ongoing research, its applications are expected to expand further, solidifying its position as a key player in modern science.

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