40311-13-5 | 6-FLUORO-2-METHYLINDOLE

CAS:40311-13-5 | 6-FLUORO-2-METHYLINDOLE,Description

The compound 6-fluoro-2-methyl-1H-indole is a fluorinated indole derivative, which is a class of compounds known for their significance in medicinal chemistry due to their presence in a variety of pharmacologically active molecules. While the provided papers do not directly discuss 6-fluoro-2-methyl-1H-indole, they do provide insights into the synthesis and reactivity of closely related fluorinated indole derivatives, which can be informative for understanding the properties and potential synthetic routes for the compound .

Synthesis Analysis

The synthesis of fluorinated indole derivatives is of considerable interest due to their potential applications. The paper titled "Synthesis and reactivity of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole"describes the preparation of N-1 BOC protected precursors of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole, followed by deprotection via flash vacuum thermolysis. This method could potentially be adapted for the synthesis of 6-fluoro-2-methyl-1H-indole by modifying the starting materials and reaction conditions to introduce a methyl group at the 2-position of the indole ring.

Molecular Structure Analysis

The molecular structure of fluorinated indoles is characterized by the presence of a fluorine atom, which can significantly influence the electronic properties of the molecule due to its high electronegativity. The stability of the unprotected indole derivatives mentioned insuggests that the introduction of fluorine at the 6-position of the indole ring can be stable under certain conditions. This information is relevant for understanding the molecular structure of 6-fluoro-2-methyl-1H-indole, as the presence of the fluorine atom is likely to affect its electronic configuration and reactivity.

Chemical Reactions Analysis

The reactivity of fluorinated indoles can vary depending on the position and number of fluorine atoms present. In the context of 6-fluoro-2-methyl-1H-indole, the fluorine atom at the 6-position could influence the reactivity of the molecule, particularly in electrophilic aromatic substitution reactions. The synthesis of methyl 5-chloro-4-fluoro-1H-indole-2-carboxylate described ininvolves regioselective iodination, which could be a relevant reaction for modifying the 6-fluoro-2-methyl-1H-indole scaffold at other positions on the ring.

Physical and Chemical Properties Analysis

The physical and chemical properties of 6-fluoro-2-methyl-1H-indole can be inferred from the properties of similar compounds. The stability and reactivity of the compounds studied inprovide a basis for predicting the behavior of 6-fluoro-2-methyl-1H-indole under various conditions. Additionally, the synthetic routes described infor 6-fluoro-7-substituted indole derivatives highlight the influence of fluorine on the chemical properties of these molecules, which is likely to extend to 6-fluoro-2-methyl-1H-indole as well.

Scientific Research Applications

Synthesis and Biological Evaluation

6-Fluoro-2-methyl-1H-indole derivatives exhibit a range of biological activities. A study focused on synthesizing various 2-(substituted phenyl)-1H-indoles, including those with fluoro groups, demonstrated their potential in anti-inflammatory, antioxidant, and antimicrobial activities. The compounds were evaluated against cytokines and tested for antimicrobial activity using the well-diffusion method. This research highlights the utility of 6-fluoro-2-methyl-1H-indole in the development of new therapeutic agents with diverse biological activities (T. Sravanthi, S. Rani, & S. L. Manju, 2015).

Photophysical Studies and Fluorescent Probes

Indole derivatives, including those with fluoro substitutions, have been studied for their photophysical properties. These compounds display high fluorescence quantum yields and solvent sensitivity in their fluorescence emission, indicating their potential as fluorescent probes. The response of these compounds to fluoride ions was evaluated, revealing their selectivity and potential application in fluorescent sensing technologies (G. Pereira, E. M. Castanheira, P. Ferreira, & M. Queiroz, 2010).

Antibiofilm and Antivirulence Properties

Indole derivatives, such as 6-fluoroindole, have been investigated for their antibiofilm and antivirulence properties against bacterial pathogens like Serratia marcescens. These compounds can interfere with quorum sensing systems and suppress biofilm formation, motility, and virulence factor production in bacteria, indicating their potential application in combating bacterial infections and reducing antibiotic resistance (S. Sethupathy, E. Sathiyamoorthi, Y.‐Guy Kim, J.‐Hyung Lee, & Jintae Lee, 2020).

Safety And Hazards

The compound is associated with certain hazards. It has been assigned the signal word “Warning” and the hazard statements H302+H312+H332, indicating that it is harmful if swallowed, in contact with skin, or if inhaled.

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