Cas no 957345-37-8 (2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine)

2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine is a halogenated pyridine derivative with a unique substitution pattern, offering versatile reactivity for synthetic applications. The presence of fluorine and iodine at the 2- and 4-positions, along with a trifluoromethyl group at the 6-position, makes it a valuable intermediate in pharmaceutical and agrochemical synthesis. The electron-withdrawing trifluoromethyl group enhances stability and influences regioselectivity in cross-coupling reactions, while the iodine substituent facilitates further functionalization via metal-catalyzed transformations. Its structural features enable precise modifications, making it useful in the development of bioactive compounds and advanced materials. The compound's high purity and well-defined reactivity profile ensure consistent performance in demanding synthetic workflows.
2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine structure
957345-37-8 structure
Product Name:2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine
CAS No:957345-37-8
MF:C6H2F4IN
MW:290.984867572784
MDL:MFCD15526901
CID:1012022
PubChem ID:53417048
Update Time:2025-10-28

2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine
    • 2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine (ACI)
    • DTXSID30697225
    • DB-330328
    • 957345-37-8
    • SCHEMBL1674054
    • CS-0530694
    • MDL: MFCD15526901
    • Inchi: 1S/C6H2F4IN/c7-5-2-3(11)1-4(12-5)6(8,9)10/h1-2H
    • InChI Key: CCDJZXRRHMOHBL-UHFFFAOYSA-N
    • SMILES: FC1C=C(I)C=C(C(F)(F)F)N=1

Computed Properties

  • Exact Mass: 290.91681g/mol
  • Monoisotopic Mass: 290.91681g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 160
  • 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: 2.9
  • Topological Polar Surface Area: 12.9?2

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2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane ;  10 min, < -65 °C; 5 min, < -65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  -65 °C → rt
Reference
Imidazolopyrazine compounds as MAPKAPK5 inhibitors useful for the treatment of degenerative and inflammatory diseases and their preparation
, World Intellectual Property Organization, , ,

2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine Raw materials

2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine Preparation Products

Additional information on 2-Fluoro-4-iodo-6-(trifluoromethyl)pyridine

2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine: A Comprehensive Overview

2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine is a highly specialized organic compound with the CAS number 957345-37-8. This compound belongs to the class of pyridine derivatives, which are widely studied in various fields of chemistry due to their unique electronic properties and potential applications in drug discovery, agrochemicals, and materials science. The structure of this compound features a pyridine ring substituted with three distinct groups: a fluoro group at position 2, an iodo group at position 4, and a trifluoromethyl group at position 6. These substituents significantly influence the compound's chemical reactivity, stability, and biological activity.

The synthesis of 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine typically involves multi-step organic reactions, often utilizing halogenation and substitution techniques. Recent advancements in catalytic methods have enabled more efficient and selective syntheses of such complex pyridine derivatives. For instance, the use of palladium-catalyzed cross-coupling reactions has become a cornerstone in constructing these compounds with high precision. Researchers have also explored the application of microwave-assisted synthesis to accelerate reaction times while maintaining product purity.

One of the most promising applications of 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine lies in its potential as a building block for drug development. The trifluoromethyl group is known to enhance lipophilicity and metabolic stability, making it an attractive feature for medicinal chemists. Recent studies have demonstrated that this compound can serve as a precursor for designing inhibitors targeting various enzymes implicated in diseases such as cancer and neurodegenerative disorders. For example, its derivatives have shown potential as kinase inhibitors, which are crucial for modulating cellular signaling pathways.

In addition to its role in drug discovery, 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine has garnered attention in agrochemical research. The presence of halogen substituents (fluoro and iodo) confers unique electronic properties that can be exploited in designing pesticides and herbicides. Recent investigations have highlighted its ability to act as a lead compound for developing novel fungicides with enhanced efficacy and reduced environmental impact. These findings underscore the importance of exploring such pyridine derivatives for sustainable agricultural solutions.

The electronic properties of 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine make it an intriguing candidate for materials science applications. Its ability to act as an electron-deficient aromatic system renders it suitable for use in organic electronics, such as light-emitting diodes (LEDs) and field-effect transistors (FETs). Researchers have recently reported on the integration of this compound into conjugated polymers, demonstrating improved charge transport properties. Such advancements pave the way for its utilization in next-generation electronic devices.

From a structural standpoint, the steric and electronic effects introduced by the fluoro, iodo, and trifluoromethyl groups create a highly functionalized pyridine derivative. Computational studies have revealed that these substituents significantly alter the molecule's π-system, enhancing its reactivity towards nucleophilic aromatic substitution reactions. This property is particularly valuable in organic synthesis, where such reactivity can be harnessed to construct complex molecular architectures.

Recent breakthroughs in analytical techniques have also contributed to a deeper understanding of 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine's properties. Advanced spectroscopic methods, such as nuclear magnetic resonance (NMR) and mass spectrometry (MS), have enabled precise characterization of this compound. Additionally, density functional theory (DFT) calculations have provided insights into its electronic structure and reactivity at the molecular level.

In conclusion, 2-Fluoro-4-Iodo-6-(Trifluoromethyl)Pyridine stands out as a versatile compound with diverse applications across multiple disciplines. Its unique combination of substituents offers immense potential for innovation in drug discovery, agrochemicals, and materials science. As research continues to uncover new avenues for its utilization, this compound is poised to play a pivotal role in advancing modern chemical sciences.

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