3093-97-8 | 6-Fluoroindole-2-carboxylic acid

CAS:3093-97-8 | 6-Fluoroindole-2-carboxylic acid,Description

6-Fluoroindole-2-carboxylic acid is a fluorinated heteroaromatic compound that is part of a broader class of indole derivatives. These compounds are of significant interest due to their diverse range of biological activities and their potential applications in pharmaceuticals. The presence of the fluorine atom can significantly alter the physical, chemical, and biological properties of these molecules.

Synthesis Analysis

The synthesis of fluorinated indoles, such as 6-fluoroindole-2-carboxylic acid, can be achieved through various methods. One approach involves the decarboxylative fluorination of electron-rich heteroaromatic carboxylic acids using Selectfluor, which has been shown to be effective for synthesizing monofluorinated indoles. Another method includes the total synthesis of related compounds like 6-fluoroindan-1-carboxylic acid, which was synthesized from 3-fluorobenzaldehyde through a multi-step process. These methods highlight the versatility and adaptability of synthetic strategies to incorporate fluorine into complex aromatic systems.

Molecular Structure Analysis

The molecular structure of fluorinated aromatic compounds is often characterized by the presence of intramolecular hydrogen bonds and the competition between different atoms as proton acceptors. For instance, in 6-fluorosalicylic acid, the fluorine atom competes with oxygen for the COOH proton, affecting the conformational equilibrium. Although this study does not directly address 6-fluoroindole-2-carboxylic acid, it provides insight into the structural dynamics that fluorine can induce in similar compounds.

Chemical Reactions Analysis

Fluorinated indoles can participate in various chemical reactions, often leading to the formation of complex structures with potential biological activity. For example, the synthesis of pyridonecarboxylic acids as antibacterial agents involves the introduction of a fluorine atom at the 6-position of the naphthyridine ring, which is structurally related to indole. The reactivity of the fluorine atom can thus be exploited to create new compounds with enhanced biological properties.

Physical and Chemical Properties Analysis

The introduction of a fluorine atom into the indole ring can significantly alter the physical and chemical properties of the compound. Fluorination can affect the pKa, viscosity, polarity, and molecular conformation of the molecule. These changes can have profound effects on the bioactivity and pharmacokinetic profile of the compound, making fluorinated indoles valuable in drug design and development.

Scientific Research Applications

Neuropharmacology

6-Fluoroindole-2-carboxylic acid has been studied in relation to its effects on the central nervous system, specifically as an antagonist of the glycine site within the NMDA receptor complex. Research indicates its potential to influence seizure thresholds and interact with conventional antiepileptic drugs (Kaminski et al., 1998).

Materials Science

In the field of materials science, derivatives of fluoroindole, like 5-fluoroindole, have been utilized to develop high-performance charge storage materials. These materials show promise for applications in supercapacitors, demonstrating superior electrochemical properties compared to other fluoropolymers (Wang et al., 2019).

Environmental Chemistry

The biodegradation of fluorotelomer surfactants, which include derivatives of fluoroindole, has been a topic of interest in environmental chemistry. Studies focus on how these substances break down in various environments and the production of degradation products like fluorotelomer carboxylic acids (D’Agostino & Mabury, 2017) .

Organic Chemistry

In organic chemistry, the fluorination of heteroaromatic carboxylic acids, including fluoroindole carboxylic acids, has been explored. Research in this area contributes to the development of methods for synthesizing fluorinated compounds, which are important in pharmaceuticals and agrochemicals (Yuan et al., 2017).

Analytical Chemistry

Fluoroindole derivatives have been investigated for their potential as fluorescent labeling reagents in analytical chemistry. This includes their application in the detection and quantification of various biochemicals in medical and environmental samples (Hirano et al., 2004).

Biomedical Research

In biomedical research, the toxicological effects of fluoroindole derivatives are studied, especially in the context of liver cell lines. This research is crucial for understanding the safety and potential health risks associated with these compounds (Sheng et al., 2017).

Pharmacology

6-Fluoroindole-2-carboxylic acid and its derivatives have been synthesized and evaluated for their analgesic activity, adding to the understanding of their potential therapeutic applications (Das et al., 2008).

Safety And Hazards

6-Fluoroindole-2-carboxylic acid may cause skin and eye irritation. It’s recommended to avoid contact with skin and eyes, and not to breathe dust.

Future Directions

6-Fluoroindole-2-carboxylic acid can be used to synthesize triindoles, via a palladium-catalyzed decarboxylative reaction. Triindoles are used as semiconductors in OFETs with a field effect mobility of 0.03 cm^2 V^-1 S^-1, as well as hole transport layers in solar cells. This suggests potential future applications in the field of electronics and renewable energy.

More Information