399-72-4 | 5-Fluoro-2-methylindole

CAS:399-72-4 | 5-Fluoro-2-methylindole,Description

5-Fluoro-2-methylindole is a fluorinated indole derivative, a class of compounds known for their presence in various biological systems and potential therapeutic applications. The presence of the fluorine atom at the 5-position on the indole ring can significantly alter the chemical and physical properties of the molecule, potentially leading to unique biological activities.

Synthesis Analysis

The synthesis of 5-fluoroindole derivatives has been explored in various studies. For instance, 5-fluoroindole was prepared from m-fluorotoluene in a multi-step process with a 46% overall yield, demonstrating the feasibility of synthesizing such compounds. Additionally, environmentally friendly methods have been employed using heterogeneous catalysts for the synthesis of 5-fluoroindoline-2,3-diones, highlighting the advancement in synthetic methodologies for these compounds.

Molecular Structure Analysis

The molecular structure of 5-fluoroindole has been studied using rotationally resolved spectroscopy, revealing the structure and electronic properties of the ground state and the lowest excited singlet state. The character of the excited state was identified as L(b), which provides insights into the photophysical behavior of the molecule.

Chemical Reactions Analysis

5-Fluoroindole derivatives have been shown to participate in various chemical reactions. For example, 5-fluoroindole-3-acetic acid is oxidized by horseradish peroxidase, forming cytotoxic products that suggest potential for targeted cancer therapy. Furthermore, the reactivity of 5-fluoroindole with different reagents has been explored, such as the formation of a covalent complex with thymidylate synthetase, which is significant in the context of biochemical pathways.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-fluoroindole derivatives are influenced by the presence of the fluorine atom. The fluorine substitution can affect the molecule's acidity, basicity, and overall reactivity. For instance, the oxidation chemistry of 5,6-dihydroxy-2-methylindole has been studied, showing rapid oxidation by the peroxidase/H2O2 system to yield a complex mixture of oligomers. Additionally, the synthesis and reactions of 2-pentafluorophenyl-5-/6-fluoroindoles have been reported, which further contributes to the understanding of the chemical behavior of fluorinated indoles.

Scientific Research Applications

• Scientific Field: Organic Chemistry and Pharmacology

  • Indoles are a significant heterocyclic system in natural products and drugs. They play a main role in cell biology. The application of indole derivatives as biologically active compounds for the treatment of cancer cells, microbes, and different types of disorders in the human body has attracted increasing attention in recent years.
  • Indole is a signalling molecule produced both by bacteria and plants. Besides the natural roles, indole also has value for flavour and fragrance applications, for example, in food industry or perfumery.

• Application Summary

  • Indoles, both natural and synthetic, show various biologically vital properties. Owing to the importance of this significant ring system, the investigation of novel methods of synthesis have attracted the attention of the chemical community.
  • Indole can be derivatized to several halogenated and oxygenated compounds that can be used as natural colourants or have promising bioactivity with therapeutic potential to treat human diseases.

• Methods of Application or Experimental Procedures

  • The Fischer indole synthesis of the optically active cyclohexanone and phenylhydrazine hydrochloride by using methanesulfonic acid (MsOH) under reflux in MeOH gave the corresponding tricyclic indole in a good yield.
  • Biocatalytic approaches have been developed to convert indole into halogenated and oxygenated derivatives.

• Results or Outcomes

  • Indole derivatives have shown potential for the treatment of cancer cells, microbes, and different types of disorders in the human body.
  • Halogenated and oxygenated derivatives of indole have promising bioactivity with therapeutic potential to treat human diseases.

Safety And Hazards

5-Fluoro-2-methylindole is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Safety measures include washing face, hands, and any exposed skin thoroughly after handling, wearing protective gloves/clothing/eye protection/face protection, and using only outdoors or in a well-ventilated area.

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