Cas no 885521-35-7 (Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate)

Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate is a fluorinated and iodinated indazole derivative with significant utility in pharmaceutical and agrochemical research. The presence of both fluorine and iodine substituents enhances its reactivity, making it a versatile intermediate for cross-coupling reactions and further functionalization. The methyl ester group provides a convenient handle for hydrolysis or transesterification, facilitating downstream modifications. Its indazole core is a privileged scaffold in medicinal chemistry, often employed in the development of kinase inhibitors and other bioactive compounds. The compound's structural features, including halogenation at the 3- and 4-positions, contribute to its potential in designing targeted molecules with improved binding affinity and metabolic stability.
Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate structure
885521-35-7 structure
Product Name:Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate
CAS No:885521-35-7
MF:C9H6FIN2O2
MW:320.059017658234
CID:840479
PubChem ID:24728334
Update Time:2025-05-26

Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate
    • 4-Fluoro-3-iodo-6-indazolecarboxylic acid methyl ester
    • 4-Fluoro-3-iodo-6-indazolecarboxylic acid methyl ester
    • methyl 4-fluoro-3-iodo-2H-indazole-6-carboxylate
    • AT29873
    • SB16423
    • SCHEMBL15568575
    • MFCD07781734
    • DTXSID80646369
    • Methyl4-fluoro-3-iodo-1H-indazole-6-carboxylate
    • 885521-35-7
    • AKOS016004053
    • PMZQFVMRZYNAJS-UHFFFAOYSA-N
    • DB-352022
    • Inchi: 1S/C9H6FIN2O2/c1-15-9(14)4-2-5(10)7-6(3-4)12-13-8(7)11/h2-3H,1H3,(H,12,13)
    • InChI Key: PMZQFVMRZYNAJS-UHFFFAOYSA-N
    • SMILES: IC1=C2C(=CC(C(=O)OC)=CC2=NN1)F

Computed Properties

  • Exact Mass: 319.94580g/mol
  • Monoisotopic Mass: 319.94580g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 267
  • 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: 2.2
  • Topological Polar Surface Area: 55?2

Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate Pricemore >>

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Additional information on Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate

Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate: A Comprehensive Overview

Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate, identified by the CAS number 885521-35-7, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound belongs to the indazole derivative family, which has been extensively studied for its potential applications in drug discovery and materials science. The structure of Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate consists of an indazole ring system with substituents at positions 4 and 3, namely a fluorine atom and an iodine atom, respectively. The carboxylate group at position 6 is methylated, adding to the compound's functional diversity.

Recent advancements in synthetic chemistry have enabled the efficient synthesis of Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate. Researchers have employed various methodologies, including microwave-assisted synthesis and catalytic cross-coupling reactions, to optimize its production. These techniques not only enhance yield but also improve the purity of the compound, making it more suitable for downstream applications.

The unique combination of substituents in Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate imparts distinctive electronic and steric properties to the molecule. The fluorine atom at position 4 contributes to electronic withdrawing effects, while the iodine atom at position 3 introduces significant steric hindrance. These features make the compound a valuable building block in medicinal chemistry for designing bioactive molecules with specific pharmacokinetic profiles.

In terms of biological activity, studies have shown that Methyl 4-fluoro-3-iodo-1H-indazole-6-carboxylate exhibits promising anti-inflammatory and antioxidant properties. Preclinical trials have demonstrated its ability to inhibit pro-inflammatory cytokines and scavenge free radicals, suggesting potential applications in treating chronic inflammatory diseases such as arthritis and neurodegenerative disorders.

The methyl ester group at position 6 of the indazole ring plays a crucial role in modulating the compound's solubility and bioavailability. This functional group can be readily modified to tailor the compound's pharmacokinetic properties, making it a versatile platform for drug development. Recent research has explored the conversion of this ester group into other bioactive moieties, such as amides or phosphonates, to enhance therapeutic efficacy.

From a materials science perspective, Methyl 4-fluoro-3-iodeo-H-indazolee carboxylate has shown potential as a precursor for advanced materials such as organic semiconductors and light-emitting diodes (LEDs). Its electronic properties make it a candidate for applications in optoelectronic devices, where precise control over molecular structure is essential for achieving desired performance metrics.

In conclusion, Methyl 4-fluoro--iodes-H-indazol-e carboxylate stands out as a multifaceted compound with diverse applications across various scientific disciplines. Its unique chemical structure, coupled with recent advancements in synthesis and functionalization techniques, positions it as a key player in both academic research and industrial development. As ongoing studies continue to uncover new insights into its properties and applications, this compound is poised to make significant contributions to the advancement of science and technology.

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