Cas no 1214622-53-3 (3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid)

3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid is a fluorinated benzoic acid derivative featuring a pyrazole substituent at the ortho position. This compound is of interest in pharmaceutical and agrochemical research due to its unique structural motif, which combines a carboxylic acid functionality with a heterocyclic group and fluorine substitution. The presence of fluorine enhances metabolic stability and bioavailability, while the pyrazole ring contributes to potential hydrogen bonding interactions, making it a versatile intermediate in drug discovery. Its well-defined chemical properties and synthetic accessibility facilitate its use in the development of biologically active molecules, particularly in the design of enzyme inhibitors or receptor modulators.
3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid structure
1214622-53-3 structure
Product Name:3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid
CAS No:1214622-53-3
MF:C10H7FN2O2
MW:206.173185586929
MDL:MFCD09054733
CID:3047461
PubChem ID:53409752
Update Time:2025-11-02

3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid
    • Benzoic acid, 3-fluoro-2-(1H-pyrazol-1-yl)-
    • 3-fluoro-2-pyrazol-1-ylbenzoic acid
    • 1214622-53-3
    • AKOS011943155
    • 3-FLUORO-2-(1H-PYRAZOL-1-YL)BENZOICACID
    • DA-47158
    • WHPUSKHJEBOLKR-UHFFFAOYSA-N
    • DTXSID901274687
    • SCHEMBL1586750
    • MDL: MFCD09054733
    • Inchi: 1S/C10H7FN2O2/c11-8-4-1-3-7(10(14)15)9(8)13-6-2-5-12-13/h1-6H,(H,14,15)
    • InChI Key: WHPUSKHJEBOLKR-UHFFFAOYSA-N
    • SMILES: C(O)(=O)C1=CC=CC(F)=C1N1C=CC=N1

Computed Properties

  • Exact Mass: 206.04915563g/mol
  • Monoisotopic Mass: 206.04915563g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 250
  • 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
  • XLogP3: 1.5
  • Topological Polar Surface Area: 55.1?2

3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid Pricemore >>

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Additional information on 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid

Recent Advances in the Study of 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid (CAS: 1214622-53-3)

3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid (CAS: 1214622-53-3) is a fluorinated benzoic acid derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its unique structural features and potential therapeutic applications. Recent studies have explored its role as a versatile scaffold for the development of novel bioactive compounds, particularly in the context of enzyme inhibition and receptor modulation.

One of the most notable findings in recent research is the compound's ability to act as a potent inhibitor of specific kinases involved in inflammatory pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid exhibited high selectivity for JAK3 kinase, a key player in autoimmune diseases. The study highlighted the compound's favorable pharmacokinetic properties, including good oral bioavailability and metabolic stability, making it a promising candidate for further drug development.

In addition to its kinase inhibitory activity, recent investigations have also explored the compound's potential as a building block for the synthesis of novel PROTACs (Proteolysis Targeting Chimeras). A 2024 preprint on bioRxiv described the successful incorporation of 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid into a PROTAC design targeting BET proteins, showing enhanced degradation efficiency compared to traditional ligands. This application opens new avenues for targeted protein degradation therapies in oncology.

The synthetic accessibility of 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid has also been a focus of recent methodological developments. A team from MIT reported in Organic Letters (2024) an improved Pd-catalyzed coupling protocol that allows for the efficient gram-scale production of the compound with excellent yield and purity. This advancement addresses previous challenges in large-scale synthesis and supports broader investigation of its medicinal applications.

Looking forward, the unique combination of fluorine substitution and pyrazole moiety in 3-Fluoro-2-(1H-pyrazol-1-yl)benzoic acid continues to inspire novel drug discovery efforts. Several pharmaceutical companies have included derivatives of this compound in their preclinical pipelines for indications ranging from inflammatory disorders to certain cancers. The coming years are likely to see more translational research bridging the gap between its promising biochemical properties and clinical applications.

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