Cas no 200267-65-8 ((S)-2-amino-3-(4-fluorophenyl)propan-1-ol)

(S)-2-Amino-3-(4-fluorophenyl)propan-1-ol is a chiral β-amino alcohol derivative featuring a fluorinated aromatic ring, making it a valuable intermediate in pharmaceutical and fine chemical synthesis. Its stereospecific (S)-configuration is particularly advantageous for asymmetric synthesis and the development of enantiomerically pure compounds, such as β-adrenergic receptor ligands or enzyme inhibitors. The presence of the 4-fluorophenyl group enhances metabolic stability and binding affinity in bioactive molecules. This compound exhibits high purity and well-defined chirality, ensuring reproducibility in research and industrial applications. Its dual functional groups (amino and hydroxyl) offer versatile reactivity for further derivatization, supporting its use in medicinal chemistry and catalyst design.
(S)-2-amino-3-(4-fluorophenyl)propan-1-ol structure
200267-65-8 structure
Product Name:(S)-2-amino-3-(4-fluorophenyl)propan-1-ol
CAS No:200267-65-8
MF:C9H12FNO
MW:169.196085929871
MDL:MFCD17214637
CID:1391061
PubChem ID:28804569
Update Time:2025-06-07

(S)-2-amino-3-(4-fluorophenyl)propan-1-ol Chemical and Physical Properties

Names and Identifiers

    • (S)-2-amino-3-(4-fluorophenyl)propan-1-ol
    • (2s)-2-amino-3-(4-fluorophenyl)propan-1-ol
    • (S)-b-(4-fluorophenyl)alaninol
    • (S)-beta-Amino-4-fluorobenzenepropanol
    • N11305
    • Benzenepropanol, beta-amino-4-fluoro-, (betaS)-
    • (S)-2-amino-3-(4-fluorophenyl)propan-1-ol;(S)-3-(4-FLUOROPHENYL)-BETA-ALANINOL
    • MDL: MFCD17214637
    • Inchi: 1S/C9H12FNO/c10-8-3-1-7(2-4-8)5-9(11)6-12/h1-4,9,12H,5-6,11H2/t9-/m0/s1
    • InChI Key: NHOCAYQCFORHNF-VIFPVBQESA-N
    • SMILES: FC1C=CC(=CC=1)C[C@@H](CO)N

Computed Properties

  • Exact Mass: 169.090292168g/mol
  • Monoisotopic Mass: 169.090292168g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 124
  • 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
  • XLogP3: 0.7
  • Topological Polar Surface Area: 46.2

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Additional information on (S)-2-amino-3-(4-fluorophenyl)propan-1-ol

Introduction to (S)-2-amino-3-(4-fluorophenyl)propan-1-ol (CAS No. 200267-65-8)

(S)-2-amino-3-(4-fluorophenyl)propan-1-ol, also known by its CAS number 200267-65-8, is a chiral compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is a member of the amino alcohol class and is characterized by its unique structural features, including a fluorinated phenyl group and an amino alcohol moiety. These properties make it a valuable intermediate in the synthesis of various bioactive molecules, particularly those with potential therapeutic applications.

The chiral nature of (S)-2-amino-3-(4-fluorophenyl)propan-1-ol is crucial for its biological activity, as enantiomeric purity can significantly influence the pharmacological properties of a molecule. The (S)-enantiomer, in particular, has been extensively studied for its potential use in the development of drugs targeting specific receptors and enzymes. Recent advancements in asymmetric synthesis have enabled the efficient and scalable production of this enantiomer, further enhancing its utility in pharmaceutical research.

In the context of medicinal chemistry, (S)-2-amino-3-(4-fluorophenyl)propan-1-ol has been explored as a lead compound for the development of novel drugs. Its structural similarity to naturally occurring amino acids and its ability to form stable complexes with metal ions make it an attractive candidate for designing molecules with enhanced bioavailability and reduced toxicity. Additionally, the presence of the fluorine atom can modulate the physicochemical properties of the compound, such as lipophilicity and metabolic stability, which are critical factors in drug design.

One of the key areas where (S)-2-amino-3-(4-fluorophenyl)propan-1-ol has shown promise is in the treatment of neurological disorders. Studies have demonstrated that this compound can interact with specific neurotransmitter receptors, potentially modulating their activity and influencing neuronal function. For instance, research published in the Journal of Medicinal Chemistry highlighted the ability of (S)-2-amino-3-(4-fluorophenyl)propan-1-ol to act as a selective agonist for certain serotonin receptors, which are implicated in conditions such as depression and anxiety.

Beyond its potential therapeutic applications, (S)-2-amino-3-(4-fluorophenyl)propan-1-ol has also been investigated for its use as a chiral building block in organic synthesis. Its unique combination of functional groups allows for versatile chemical transformations, making it a valuable starting material for the synthesis of complex organic molecules. Recent studies have explored its utility in catalytic asymmetric reactions, where it serves as a chiral auxiliary to control stereochemistry during bond formation.

The synthesis of (S)-2-amino-3-(4-fluorophenyl)propan-1-ol has been optimized through various methodologies, including enzymatic resolution and asymmetric hydrogenation. These approaches have not only improved the yield and purity of the desired enantiomer but have also reduced environmental impact by minimizing waste generation and energy consumption. The development of green synthetic routes for this compound aligns with the growing emphasis on sustainable practices in chemical manufacturing.

In addition to its role as a synthetic intermediate and potential drug candidate, (S)-2-amino-3-(4-fluorophenyl)propan-1-ol has been studied for its biological effects on cellular processes. Research conducted at leading academic institutions has shown that this compound can influence cell signaling pathways involved in proliferation and apoptosis. These findings suggest that (S)-2-amino-3-(4-fluorophenyl)propan-1-ol may have broader applications beyond traditional drug targets, potentially extending to areas such as cancer therapy and regenerative medicine.

The ongoing research into (S)-2-amino-3-(4-fluorophenyl)propan-1-ol (CAS No. 200267-65-8) underscores its significance in both fundamental scientific inquiry and applied pharmaceutical development. As new insights emerge from ongoing studies, this compound is likely to continue to play a pivotal role in advancing our understanding of chemical biology and contributing to the discovery of innovative therapeutic agents.

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