1352625-30-9 | 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine

CAS:1352625-30-9 | 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine,Description

3-Bromo-6-fluoropyrazolo[1,5-a]pyridine is a compound that belongs to the class of pyrazolopyridines, which are heterocyclic aromatic compounds containing both pyrazole and pyridine rings. These compounds are of interest due to their potential applications in various fields, including organic electronics, pharmaceuticals, and as intermediates in organic synthesis. The presence of bromine and fluorine atoms in the compound suggests that it could be a versatile intermediate for further chemical modifications, given the reactivity of these halogens in substitution reactions.

Synthesis Analysis

The synthesis of related pyrazolopyridine compounds has been reported using various methods. For instance, a one-pot route for the synthesis of 3-formylpyrazolo[1,5-a]pyrimidines has been developed, which proceeds via a cyclocondensation reaction followed by formylation using the Vilsmeyer-Haack reagent. Additionally, the synthesis of bipyrazolo[1,5-a]pyridine derivatives has been achieved through palladium-catalyzed cross-dehydrogenative coupling of pyrazolo[1,5-a]pyridine precursors, demonstrating good functional group tolerance and high yields. Although these methods do not directly describe the synthesis of 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, they provide insight into the synthetic strategies that could be adapted for its preparation.

Molecular Structure Analysis

The molecular structure of pyrazolopyridine derivatives has been characterized using NMR measurements and X-ray diffraction analysis. These techniques allow for the determination of the regioselectivity of the reactions and the confirmation of the structures of the synthesized compounds. The introduction of halogen atoms like bromine and fluorine can influence the electronic properties of the molecule, potentially affecting its reactivity and interaction with other molecules.

Chemical Reactions Analysis

The reactivity of pyrazolopyridine derivatives can be explored through various chemical reactions. For example, the introduction of diaryl groups onto the pyrazolopyridine skeleton has been shown to enhance the emission properties of these compounds, indicating that they can undergo further functionalization. The fluorination of methyl pyrazolo[1,5-a]pyridine-3-carboxylates to form 3-fluoropyrazolo[1,5-a]pyridines has also been studied, revealing the formation of an intermediate fluorine-containing σ-complex. These studies suggest that 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine could participate in similar reactions, potentially leading to novel compounds with interesting properties.

Physical and Chemical Properties Analysis

The physical and chemical properties of pyrazolopyridine derivatives are influenced by their molecular structure and the substituents present on the rings. For instance, the photophysical properties of pyrazolo[1,5-a]pyrimidines have been investigated, showing that they exhibit large Stokes shifts and fluorescence intensity variations depending on the solvent and substituents. The introduction of halogen atoms is likely to affect the electronic properties of the molecule, such as its dipole moment and polarizability, which in turn can influence its solubility, boiling point, and other physical properties. The presence of bromine and fluorine in 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine suggests that it may have distinct physical and chemical properties that could be exploited in various applications.

Scientific Research Applications

Synthesis and Chemical Transformations

• Synthesis Techniques : The compound is synthesized through various chemical reactions. For instance, the fluorination of methyl esters of pyrazolo[1,5-a]pyridine carboxylic acids produces fluoropyrazolo[1,5-a]pyridines (Alieva & Vorob’ev, 2020). Another method involves the reaction of sodium 3-oxoprop-1-en-1-olate with heterocyclic amines, leading to the synthesis of pyrazolo[1,5-a]pyrimidines and related compounds (Abdelriheem, Zaki, & Abdelhamid, 2017).
• Formation of Complex Structures : Gold-catalyzed and iodine-mediated cyclization of enynylpyrazoles forms pyrazolo[1,5-a]pyridines. These adducts can be further converted to various other derivatives through Suzuki-Miyaura coupling and Ullmann condensation reactions (Wu, Yang, Hwang, & Wu, 2012).

Photophysical and Biological Properties

• Photophysical Properties : A study on bipyrazolo[1,5-a]pyridines revealed their potential as fluorophores with notable intramolecular charge transfer. Modifications to these compounds can enhance their emission properties, making them suitable for applications in fluorescence and photophysics (Hsiao & Chu, 2021).
• Biological Applications : While this search focused on excluding drug use and dosage, it is notable that pyrazolo[1,5-a]pyrimidines and related structures exhibit biological activities. For example, they have shown potential in antimicrobial applications, with some derivatives exhibiting significant antibacterial properties (Abdel‐Latif, Mehdhar, & Abdel-Ghani, 2019) .

Safety And Hazards

The compound is labeled with the GHS07 pictogram and has the signal word "Warning". Hazard statements include H315, H319, and H335. Precautionary statements include P261, P305, P338, and P351.

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