Cas no 1260817-75-1 (2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride)

2-Amino-3-(4-fluorophenyl)propan-1-ol hydrochloride is a fluorinated phenylpropanolamine derivative with applications in pharmaceutical and organic synthesis. Its key structural features include a primary amine and a hydroxyl group on a propyl backbone, along with a 4-fluorophenyl substituent, enhancing its reactivity and potential as a chiral intermediate. The hydrochloride salt form improves stability and solubility, facilitating handling and storage. This compound is particularly valuable in the synthesis of bioactive molecules, including adrenergic receptor ligands and CNS-active compounds, due to its fluorine moiety, which can influence binding affinity and metabolic properties. Its well-defined stereochemistry also makes it useful for enantioselective synthesis.
2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride structure
1260817-75-1 structure
Product Name:2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride
CAS No:1260817-75-1
MF:C9H13ClFNO
MW:205.657025098801
CID:4583366
PubChem ID:53416424
Update Time:2025-05-19

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

Names and Identifiers

    • 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride
    • Inchi: 1S/C9H12FNO.ClH/c10-8-3-1-7(2-4-8)5-9(11)6-12;/h1-4,9,12H,5-6,11H2;1H
    • InChI Key: CJNPZBLHJLXNSC-UHFFFAOYSA-N
    • SMILES: C(C1C=CC(F)=CC=1)C(N)CO.Cl

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3

2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride Pricemore >>

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

Introduction to 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride (CAS No. 1260817-75-1)

2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride, identified by the chemical abstracts service number 1260817-75-1, is a significant compound in the field of pharmaceutical chemistry. This compound belongs to the class of fluorinated aromatic amines, which have garnered considerable attention due to their diverse biological activities and potential applications in drug development. The structural motif of this molecule, featuring a primary amine group, a hydroxyl group, and a fluorophenyl ring, makes it a versatile scaffold for medicinal chemists exploring novel therapeutic agents.

The hydrochloride salt form of 2-amino-3-(4-fluorophenyl)propan-1-ol enhances its solubility in aqueous solutions, which is a critical factor for its formulation in pharmaceutical applications. This solubility profile facilitates its use in various drug delivery systems, including oral and intravenous formulations. The presence of the fluorine atom at the para position of the phenyl ring introduces unique electronic and steric properties, influencing both the reactivity and binding affinity of the molecule towards biological targets.

Recent advancements in computational chemistry and molecular modeling have enabled a deeper understanding of the interactions between 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride and biological macromolecules. Studies have highlighted its potential as an intermediate in the synthesis of kinase inhibitors, particularly those targeting tyrosine kinases involved in cancer therapy. The fluorine substituent has been shown to improve metabolic stability and binding affinity, making it an attractive moiety for drug design.

In vitro studies have demonstrated that derivatives of this compound exhibit inhibitory effects on several kinases, including Janus kinases (JAKs) and platelet-derived growth factor receptors (PDGFRs). These kinases are aberrantly activated in various inflammatory and proliferative diseases, making them promising targets for therapeutic intervention. The structural flexibility of 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride allows for modifications that can fine-tune its pharmacological properties, such as selectivity and potency.

The role of fluorine atoms in medicinal chemistry is well-documented, with numerous examples where fluorination has led to enhanced drug efficacy. For instance, fluoroaromatic compounds often exhibit improved bioavailability due to their increased lipophilicity and resistance to metabolic degradation. The 4-fluorophenyl group in 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride contributes to these favorable properties, making it a valuable component in drug discovery efforts.

Current research is exploring the use of this compound as a building block for more complex molecules with enhanced therapeutic profiles. By incorporating it into larger scaffolds, chemists aim to develop novel agents that can address unmet medical needs more effectively. The primary amine and hydroxyl groups provide multiple sites for further functionalization, allowing for the creation of diverse chemical entities with tailored biological activities.

The synthesis of 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride involves multi-step organic reactions that require precise control over reaction conditions. Advanced synthetic methodologies, such as transition metal-catalyzed cross-coupling reactions and asymmetric hydrogenations, have been employed to achieve high yields and enantioselectivity. These techniques are essential for producing enantiomerically pure forms of the compound, which are crucial for pharmaceutical applications where stereochemistry plays a critical role.

Pharmacokinetic studies have been conducted to evaluate the absorption, distribution, metabolism, and excretion (ADME) properties of 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride. These studies provide valuable insights into how the compound behaves within the body and guide its optimization for clinical use. For example, understanding its metabolic pathways helps in predicting potential drug-drug interactions and adverse effects.

The development of novel therapeutic agents often involves collaboration between synthetic chemists, pharmacologists, and bioinformaticians. By leveraging computational tools to predict biological activity and optimize molecular structures, researchers can accelerate the discovery process. 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride serves as a prime example of how interdisciplinary approaches can lead to breakthroughs in drug design.

In conclusion, 2-amino-3-(4-fluorophenyl)propan-1-ol hydrochloride (CAS No. 1260817-75-1) is a promising compound with significant potential in pharmaceutical research. Its unique structural features make it an excellent candidate for developing new drugs targeting various diseases. Ongoing studies continue to uncover its therapeutic applications, reinforcing its importance as a key intermediate in medicinal chemistry.

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