Cas no 2227680-24-0 ((1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol)

(1R)-3-Amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol is a chiral compound featuring a fluorinated nitrophenyl group and an amino alcohol moiety, making it a valuable intermediate in pharmaceutical and fine chemical synthesis. Its stereospecific (R)-configuration ensures high enantioselectivity in asymmetric reactions, while the presence of both amino and hydroxyl functional groups enhances its utility in derivatization and coupling reactions. The electron-withdrawing nitro and fluoro substituents on the aromatic ring further contribute to its reactivity in nucleophilic substitution and reduction processes. This compound is particularly useful in the development of bioactive molecules, including CNS-targeting agents and enzyme inhibitors, due to its structural versatility and synthetic accessibility.
(1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol structure
2227680-24-0 structure
Product Name:(1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol
CAS No:2227680-24-0
MF:C9H11FN2O3
MW:214.193645715714
CID:5900808
PubChem ID:165757355
Update Time:2025-11-02

(1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol Chemical and Physical Properties

Names and Identifiers

    • (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol
    • EN300-1805338
    • 2227680-24-0
    • Inchi: 1S/C9H11FN2O3/c10-7-5-6(9(13)3-4-11)1-2-8(7)12(14)15/h1-2,5,9,13H,3-4,11H2/t9-/m1/s1
    • InChI Key: HSYFXDYXAHZSHO-SECBINFHSA-N
    • SMILES: FC1=C(C=CC(=C1)[C@@H](CCN)O)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 214.07537038g/mol
  • Monoisotopic Mass: 214.07537038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 222
  • 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: 0.4
  • Topological Polar Surface Area: 92.1?2

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Additional information on (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol

Comprehensive Analysis of (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol (CAS No. 2227680-24-0)

The compound (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol (CAS No. 2227680-24-0) is a chiral amino alcohol derivative with significant potential in pharmaceutical and chemical research. Its unique structure, featuring a fluoro and nitro substituent on the aromatic ring, makes it a valuable intermediate in the synthesis of bioactive molecules. Researchers are increasingly interested in this compound due to its potential applications in drug discovery, particularly in the development of central nervous system (CNS) therapeutics and enzyme inhibitors.

One of the most searched questions in scientific databases is: "What are the synthetic routes for (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol?" This reflects the growing demand for efficient and scalable synthesis methods. The compound can be prepared via asymmetric reduction of the corresponding ketone or through resolution techniques. Recent advancements in catalytic asymmetric synthesis have improved the yield and enantiomeric purity of this compound, making it more accessible for research purposes.

The pharmacological properties of (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol are another hot topic among researchers. Its structural features suggest potential interactions with G-protein coupled receptors (GPCRs) and neurotransmitter transporters. These properties align with current trends in precision medicine and targeted drug delivery, which are highly searched keywords in the pharmaceutical community. The compound's chirality is particularly important, as enantiopure drugs often exhibit superior efficacy and safety profiles.

From a chemical stability perspective, the presence of both electron-withdrawing (nitro and fluoro) and electron-donating (amino and hydroxyl) groups creates interesting reactivity patterns. This duality makes the compound a subject of study in structure-activity relationship (SAR) analyses, a frequently searched term in medicinal chemistry circles. The nitrophenyl moiety, in particular, offers opportunities for further functionalization, which is valuable in combinatorial chemistry approaches.

In the context of green chemistry - a trending topic in scientific discussions - researchers are exploring eco-friendly purification methods for (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol. Techniques like supercritical fluid chromatography and aqueous workup procedures are gaining attention as alternatives to traditional organic solvent-based methods. These approaches address the increasing demand for sustainable chemical processes in pharmaceutical manufacturing.

The compound's spectroscopic characterization is another area of interest, with many researchers searching for detailed NMR and mass spectrometry data. The fluoro substituent provides a useful 19F NMR handle for reaction monitoring, while the nitro group offers distinctive IR absorption patterns. These features make the compound particularly amenable to analytical method development, another hot topic in chemical research.

Looking at computational chemistry applications - a rapidly growing field - (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol serves as an excellent model compound for studying molecular docking and quantum mechanical calculations. The presence of multiple functional groups allows for diverse interaction patterns with biological targets, making it valuable for in silico drug design studies. This aligns with current interests in AI-assisted drug discovery, one of the most searched topics in pharmaceutical research today.

In conclusion, (1R)-3-amino-1-(3-fluoro-4-nitrophenyl)propan-1-ol (CAS No. 2227680-24-0) represents a multifaceted compound with broad research applications. Its relevance to current scientific trends - from asymmetric synthesis to computational drug design - ensures continued interest from both academic and industrial researchers. As synthetic methodologies advance and biological evaluations progress, this compound is likely to play an increasingly important role in the development of novel therapeutic agents.

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