Cas no 1158763-55-3 (5-(3-Fluorophenyl)picolinic acid)

5-(3-Fluorophenyl)picolinic acid is a fluorinated aromatic compound featuring a picolinic acid core substituted with a 3-fluorophenyl group. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The fluorine atom enhances metabolic stability and binding affinity in target molecules, while the picolinic acid moiety offers chelating capabilities for metal coordination. Its high purity and well-defined reactivity profile facilitate precise modifications in medicinal chemistry applications. The compound is particularly useful in the development of kinase inhibitors and other bioactive molecules, where its structural features contribute to improved potency and selectivity. Suitable for research and industrial-scale applications.
5-(3-Fluorophenyl)picolinic acid structure
1158763-55-3 structure
Product Name:5-(3-Fluorophenyl)picolinic acid
CAS No:1158763-55-3
MF:C12H8FNO2
MW:217.195826530457
MDL:MFCD12406462
CID:1031656
PubChem ID:46313125
Update Time:2025-08-02

5-(3-Fluorophenyl)picolinic acid Chemical and Physical Properties

Names and Identifiers

    • 5-(3-Fluorophenyl)picolinic acid
    • 5-(3-fluorophenyl)pyridine-2-carboxylic acid
    • AK126816
    • KB-243486
    • SureCN486067
    • JJDSMZVLNUOPNZ-UHFFFAOYSA-N
    • AX8169544
    • SCHEMBL486067
    • DTXSID40673419
    • AKOS012258415
    • AS-66897
    • DB-332597
    • CS-0156906
    • C71503
    • 5-(3-Fluorophenyl)picolinicacid
    • 2-Pyridinecarboxylic acid, 5-(3-fluorophenyl)-
    • MFCD12406462
    • 1158763-55-3
    • MDL: MFCD12406462
    • Inchi: 1S/C12H8FNO2/c13-10-3-1-2-8(6-10)9-4-5-11(12(15)16)14-7-9/h1-7H,(H,15,16)
    • InChI Key: JJDSMZVLNUOPNZ-UHFFFAOYSA-N
    • SMILES: FC1=CC=CC(=C1)C1C=NC(C(=O)O)=CC=1

Computed Properties

  • Exact Mass: 217.05390666g/mol
  • Monoisotopic Mass: 217.05390666g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 259
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 50.2
  • XLogP3: 2.4

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Additional information on 5-(3-Fluorophenyl)picolinic acid

Introduction to 5-(3-Fluorophenyl)picolinic Acid (CAS No. 1158763-55-3)

5-(3-Fluorophenyl)picolinic acid, identified by the Chemical Abstracts Service Number (CAS No.) 1158763-55-3, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and biochemical research. This compound belongs to the class of heterocyclic carboxylic acids, characterized by its fused ring structure containing nitrogen and a carboxylic acid functional group. The presence of a fluorophenyl substituent in its molecular framework imparts unique electronic and steric properties, making it a versatile candidate for various applications in medicinal chemistry and drug discovery.

The molecular structure of 5-(3-Fluorophenyl)picolinic acid consists of a pyridine ring connected to a benzene ring substituted with a fluorine atom at the 3-position. This architectural design not only enhances its solubility in polar solvents but also influences its interactions with biological targets. The fluorine atom, being electronegative, can modulate the electronic distribution across the molecule, potentially affecting its binding affinity and metabolic stability. Such structural features are highly valued in the development of novel therapeutic agents, where precise tuning of physicochemical properties is crucial for optimizing drug efficacy and pharmacokinetics.

In recent years, 5-(3-Fluorophenyl)picolinic acid has been extensively studied for its potential applications in the synthesis of pharmacologically active compounds. Its pyridine core is a common motif in many bioactive molecules, serving as a scaffold for further functionalization. Researchers have explored its utility in designing inhibitors targeting various enzymatic pathways implicated in diseases such as cancer, inflammation, and neurodegeneration. The fluorophenyl moiety, in particular, has been shown to enhance the metabolic stability and binding interactions of drug candidates, contributing to their improved pharmacological profiles.

One of the most compelling aspects of 5-(3-Fluorophenyl)picolinic acid is its role as a precursor in the synthesis of more complex molecules. For instance, it has been utilized in the preparation of fluorinated heterocycles, which are known to exhibit enhanced bioavailability and reduced toxicity compared to their non-fluorinated counterparts. The compound’s ability to undergo selective functionalization at multiple sites allows chemists to tailor its properties for specific applications. This flexibility makes it an indispensable tool in medicinal chemistry laboratories striving to develop next-generation therapeutics.

Recent advancements in computational chemistry have further highlighted the significance of 5-(3-Fluorophenyl)picolinic acid in drug design. Molecular modeling studies have demonstrated that the fluorine atom can act as an anchor point for hydrogen bonding interactions with biological targets, thereby improving drug-receptor binding affinity. Additionally, the compound’s aromaticity and planar structure contribute to favorable pharmacokinetic properties, such as improved oral bioavailability and reduced clearance rates. These insights have spurred interest in exploring its potential as an intermediate in the development of small-molecule drugs with enhanced therapeutic efficacy.

The pharmaceutical industry has taken note of these promising attributes, leading to several ongoing clinical trials where derivatives of 5-(3-Fluorophenyl)picolinic acid are being evaluated for their therapeutic potential. Preliminary results suggest that certain analogs exhibit significant anti-inflammatory and anticancer activities without compromising safety margins. These findings underscore the importance of this compound as a building block for innovative drug candidates targeting critical disease pathways.

Beyond pharmaceutical applications, 5-(3-Fluorophenyl)picolinic acid has found utility in agrochemical research, where fluorinated compounds are increasingly preferred for their improved resistance to degradation and enhanced biological activity. Its incorporation into pesticide formulations has shown promise in reducing environmental persistence while maintaining efficacy against pests. This dual functionality highlights the compound’s broad applicability across multiple scientific domains.

The synthesis of 5-(3-Fluorophenyl)picolinic acid itself presents an interesting challenge due to the need for precise control over reaction conditions to achieve high yields and purity. Advanced synthetic methodologies, including transition-metal-catalyzed cross-coupling reactions and fluorochemical transformations, have been employed to streamline its production. These techniques not only improve efficiency but also enable access to structurally diverse derivatives for further investigation.

In conclusion,5-(3-Fluorophenyl)picolinic acid (CAS No. 1158763-55-3) represents a fascinating compound with multifaceted applications in pharmaceuticals and agrochemicals. Its unique structural features and versatile reactivity make it a valuable asset in drug discovery efforts aimed at addressing unmet medical needs. As research continues to uncover new therapeutic possibilities,fluorophenyl-containing picolinic acid derivatives are poised to play an increasingly pivotal role in shaping the future of medicine.

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