Cas no 114873-10-8 (Boc-D-2-Fluorophenylalanine)

Boc-D-2-Fluorophenylalanine is a protected derivative of D-2-fluorophenylalanine, featuring a tert-butoxycarbonyl (Boc) group at the amino terminus. This compound is widely utilized in peptide synthesis, particularly in the preparation of fluorinated peptides, where the Boc group serves as a temporary protecting group for the amine functionality. The incorporation of a fluorine atom at the ortho position of the phenyl ring enhances steric and electronic properties, making it valuable in medicinal chemistry and drug development. Its high purity and stability under standard peptide coupling conditions ensure reliable performance in solid-phase and solution-phase synthesis. The product is suitable for research applications requiring fluorinated amino acid analogs.
Boc-D-2-Fluorophenylalanine structure
Boc-D-2-Fluorophenylalanine structure
Product Name:Boc-D-2-Fluorophenylalanine
CAS No:114873-10-8
MF:C14H18FNO4
MW:283.295427799225
MDL:MFCD00672521
CID:63116
PubChem ID:7020833
Update Time:2025-06-08

Boc-D-2-Fluorophenylalanine Chemical and Physical Properties

Names and Identifiers

    • (R)-2-((tert-Butoxycarbonyl)amino)-3-(2-fluorophenyl)propanoic acid
    • BOC-2-fluoro-D-phenylalanine
    • BOC-D-Phe(2-F)-OH
    • tert-Butoxycarbonyl-D-2-fluorophenylalanine
    • (R)-N-BOC-2-Fluorophenylalanine
    • Boc-D-2-Fluorophe
    • Boc-D-2-Fluorophenylalanine
    • BOC-D-PHE(O-F)-OH
    • BOC-2-FLUORO-D-PHE
    • RARECHEM BK PT 0023
    • BOC-O-FLUORO-D-PHE-OH
    • Boc-D-2-Fluoro-phe-OH
    • PS-12132
    • MFCD00672521
    • N-alpha-t-Butyloxycarbonyl-D-2-fluorophenylalanine (Boc-D-Phe(2-F)-OH)
    • N10787
    • N-tert-Butoxycarbonyl-D-2-Fluoro Phenylalanine
    • J-003147
    • AKOS015994903
    • SCHEMBL270318
    • (R)-2-(tert-butoxycarbonylamino)-3-(2-fluorophenyl)propanoic acid
    • (2R)-3-(2-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
    • 114873-10-8
    • (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID
    • DTXSID60427299
    • AM83331
    • NTWUXBKUDXGMHV-LLVKDONJSA-N
    • Boc-D-Phe(2-F)-OH, >=98.0% (TLC)
    • CS-W012252
    • EN300-2010708
    • (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(2-fluorophenyl)propanoic acid
    • Boc-L-phe(2-F)-OH
    • N-(tert-butoxycarbonyl)-2-fluoro-D-phenylalanine
    • (R)-2-tert-butoxycarbonylamino-3-(2-fluorophenyl)propionic acid
    • AC-5823
    • D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-2-fluoro-
    • CHEMBL5305671
    • (2R)-2-[(tert-butoxycarbonyl)amino]-3-(2-fluorophenyl)propanoic acid
    • MDL: MFCD00672521
    • Inchi: 1S/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1
    • InChI Key: NTWUXBKUDXGMHV-LLVKDONJSA-N
    • SMILES: FC1C=CC=CC=1C[C@H](C(=O)O)NC(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 283.12200
  • Monoisotopic Mass: 283.122
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 7
  • Complexity: 354
  • 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: 75.6A^2
  • XLogP3: 2.6

Experimental Properties

  • Color/Form: No data available
  • Density: 1.1918 (estimate)
  • Melting Point: 94 oC
  • Boiling Point: 308.1°Cat760mmHg
  • Flash Point: 140.1°C
  • PSA: 75.63000
  • LogP: 2.73700
  • Specific Rotation: -10 o (c=1,EtOAc)

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Additional information on Boc-D-2-Fluorophenylalanine

Boc-D-2-Fluorophenylalanine: A Comprehensive Overview

The compound with CAS No. 114873-10-8, known as Boc-D-2-Fluorophenylalanine, is a significant molecule in the field of organic chemistry and biochemistry. This compound is a derivative of phenylalanine, a naturally occurring amino acid, with a fluorine atom substituted at the 2-position of the benzene ring. The presence of the tert-butoxycarbonyl (Boc) group further modifies its structure, making it a valuable intermediate in peptide synthesis and other chemical reactions.

Boc-D-2-Fluorophenylalanine has garnered attention due to its unique properties and potential applications in drug discovery and biotechnology. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in the context of fluorinated amino acids. Fluorination is a common strategy in drug design to enhance pharmacokinetic properties such as stability, bioavailability, and metabolic resistance. The 2-fluoro substitution in this compound provides a promising platform for exploring these attributes.

The synthesis of Boc-D-2-Fluorophenylalanine involves a multi-step process that combines principles from organic synthesis and stereochemistry. The starting material is typically L-phenylalanine, which undergoes several transformations to introduce the fluorine atom and the Boc group. Researchers have optimized these steps to achieve high yields and enantiomeric purity, ensuring that the compound meets the stringent requirements of modern pharmaceutical research.

One of the most exciting developments involving Boc-D-2-Fluorophenylalanine is its application in peptide synthesis. The Boc group serves as an excellent protecting group for the amino terminus, allowing for precise control during peptide assembly. This has enabled chemists to construct complex peptide sequences with high fidelity, paving the way for the creation of bioactive peptides with potential therapeutic applications.

Recent advancements in analytical techniques have also enhanced our understanding of Boc-D-2-Fluorophenylalanine's structural and electronic properties. For instance, nuclear magnetic resonance (NMR) spectroscopy has provided insights into its conformational flexibility, while mass spectrometry has confirmed its molecular integrity. These studies are crucial for validating the compound's suitability in various chemical and biological assays.

In terms of biological activity, Boc-D-2-Fluorophenylalanine has shown promise in modulating enzyme activity and cellular signaling pathways. Preclinical studies suggest that it may possess anti-inflammatory or neuroprotective effects, although further research is needed to confirm these findings. Its fluorinated nature could also confer resistance to enzymatic degradation, making it an attractive candidate for long-lasting drug delivery systems.

The demand for Boc-D-2-Fluorophenylalanine has been driven by its versatility across multiple disciplines. Chemists value it for its reactivity in coupling reactions, while biologists appreciate its role as a building block for constructing bioactive molecules. Its inclusion in high-throughput screening libraries has further expanded its utility in drug discovery pipelines.

From an environmental perspective, researchers have investigated the degradation pathways of Boc-D-2-Fluorophenylalanine under various conditions. Understanding its fate in natural systems is essential for assessing its potential impact on ecosystems and ensuring sustainable practices in chemical manufacturing.

In conclusion, Boc-D-2-Fluorophenylalanine stands out as a versatile and innovative compound with wide-ranging applications in chemistry and biology. Its unique structure, combined with cutting-edge research findings, positions it as a key player in advancing drug development and chemical synthesis technologies.

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