885520-35-4 | 4-BROMO-6-FLUORO (1H)INDAZOLE

CAS:885520-35-4 | 4-BROMO-6-FLUORO (1H)INDAZOLE,Description

4-Bromo-6-fluoro-1H-indazole is a derivative of the indazole heterocycle, which is characterized by a fusion of benzene and pyrazole rings. Indazole derivatives are of significant interest due to their wide range of biological activities and their applications in medicinal chemistry.

Synthesis Analysis

The synthesis of indazole derivatives can be achieved through various methods. One approach involves the regioselective metal-free preparation of azole derivatives, as described in the synthesis of fluorosulfonyl 1,2,3-triazoles from bromovinylsulfonyl fluoride. Although this paper does not directly discuss the synthesis of 4-Bromo-6-fluoro-1H-indazole, the methodology could potentially be adapted for its synthesis by using appropriate precursors and reaction conditions.

Another method for synthesizing indazole derivatives is the 1,3-dipolar cycloaddition reaction. For instance, the reaction between 3-phenylsydnone and p-toluquinone leads to the formation of 2H-indazole-4,7-dione derivatives. This paper also reports the further bromination of these compounds to yield bromo derivatives, which is relevant to the synthesis of brominated indazoles.

Molecular Structure Analysis

The molecular structure of indazole derivatives can be complex and is often determined using single-crystal X-ray diffraction. The paper on the crystal structure of 6-bromo-5-methyl-2-phenyl-2H-indazole-4,7-dione provides detailed crystallographic data, including the space group, unit cell dimensions, and the refinement of the structure. This information is crucial for understanding the three-dimensional arrangement of atoms within the molecule and can provide insights into the reactivity and properties of the compound.

Chemical Reactions Analysis

Indazole derivatives can undergo various chemical reactions, including nucleophilic substitution, which is a common method for modifying the indazole core. The synthesis of methyl 1-(4-fluorobenzyl)-1H-indazole-3-carboxylate via nucleophilic substitution of the indazole N—H hydrogen with 1-(bromomethyl)-4-fluorobenzene is an example of such a reaction. This reaction showcases the potential for functionalizing the indazole ring system to introduce different substituents, such as bromo and fluoro groups.

Physical and Chemical Properties Analysis

The physical and chemical properties of indazole derivatives are influenced by their molecular structure. The presence of halogen atoms, such as bromine and fluorine, can affect the compound's polarity, reactivity, and interaction with biological targets. The crystallographic study mentioned earlier provides valuable information on the molecular geometry, which can be related to the compound's physical properties, such as melting point, solubility, and stability. Additionally, the hydrogen-bond-like interactions observed in the crystal of methyl 1-(4-fluorobenzyl)-1H-indazole-3-carboxylate suggest that such compounds may have the potential to form specific interactions in biological systems.

Scientific Research Applications

• Phosphoinositide 3-Kinase (PI3K) Inhibitors

  • Field : Medicinal Chemistry
  • Application : 4-Bromo-6-fluoro-1H-indazole is used in the preparation of PI3 kinase inhibitors. PI3Ks are a family of enzymes involved in cellular functions such as cell growth, proliferation, differentiation, motility, survival and intracellular trafficking, which makes them an attractive target for therapeutic interventions.

• Synthesis of Indazoles

  • Field : Organic Chemistry
  • Application : 4-Bromo-6-fluoro-1H-indazole might be used in the synthesis of indazoles. Indazoles are a type of heterocyclic compound that have a wide variety of medicinal applications such as antihypertensive, anticancer, antidepressant, anti-inflammatory, and antibacterial agents.
  • Method : The strategies include transition metal catalyzed reactions, reductive cyclization reactions, and synthesis of 2H-indazoles via consecutive formation of C–N and N–N bonds without catalyst and solvent from 2-azidobenzaldehydes and amines.

• Dye-Sensitized Solar Cells (DSSCs)

  • Field : Material Science
  • Application : Indazole is a highly conjugated molecule which expands its applications to dye-sensitized solar cells (DSSCs). 4-fluoro-1H-indazole can coordinate to metal centre (such as Ir, Ln and Eu) to form either heteroleptic or homoleptic triplet photosensitizers that have an efficient ligand to metal energy transfer process.
• Preparation of PI3 Kinase Inhibitors
  • Field : Medicinal Chemistry
  • Application : 4-Bromo-6-fluoro-1H-indazole is used in the preparation of PI3 kinase inhibitors. PI3Ks are a family of enzymes involved in cellular functions such as cell growth, proliferation, differentiation, motility, survival and intracellular trafficking, which makes them an attractive target for therapeutic interventions.
• Preparation of PI3 Kinase Inhibitors
  • Field : Medicinal Chemistry
  • Application : 4-Bromo-6-fluoro-1H-indazole is used in the preparation of PI3 kinase inhibitors. PI3Ks are a family of enzymes involved in cellular functions such as cell growth, proliferation, differentiation, motility, survival and intracellular trafficking, which makes them an attractive target for therapeutic interventions.

Safety And Hazards

The safety information for 4-Bromo-6-fluoro-1H-indazole indicates that it may cause skin irritation, serious eye irritation, and respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use only outdoors or in a well-ventilated area.

Future Directions

While specific future directions for 4-Bromo-6-fluoro-1H-indazole are not mentioned, similar compounds like 4-fluoro-1H-indazole have applications in dye-sensitized solar cells (DSSCs) and can form photosensitizers that have an efficient ligand to metal energy transfer process. This suggests potential future directions in the field of energy and materials science.

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