366-99-4 | 3-Fluoro-4-methoxyaniline

CAS:366-99-4 | 3-Fluoro-4-methoxyaniline,Description

3-Fluoro-4-methoxyaniline is a chemical compound that is part of the aniline family, characterized by the presence of a methoxy group (-OCH3) and a fluorine atom attached to a benzene ring. This compound is of interest due to its potential applications in various chemical reactions and its role as a building block in organic synthesis.

Synthesis Analysis

The synthesis of 3-Fluoro-4-methoxyaniline can be achieved through several methods. One approach involves the Ullmann methoxylation reaction, where 2-fluoro-4-iodoaniline is used as a starting material. The iodine is replaced by a methoxy group to yield 3-Fluoro-4-methoxyaniline. This process involves the use of protection and deprotection steps for the nitrogen atom and the use of halogen compounds, specifically fluorine and iodine compounds.

Molecular Structure Analysis

The molecular structure of 3-Fluoro-4-methoxyaniline consists of a benzene ring with a methoxy group at the 4-position and a fluorine atom at the 3-position. The presence of these substituents can influence the electronic properties of the molecule, as well as its reactivity. The exact molecular geometry and electronic distribution would require further analysis through spectroscopic techniques or computational methods, which are not detailed in the provided papers.

Chemical Reactions Analysis

3-Fluoro-4-methoxyaniline can participate in various chemical reactions due to the presence of the aniline nitrogen, which can act as a nucleophile, and the electron-donating methoxy group, which can influence the reactivity of the fluorine atom. For instance, the photosubstitution of 2-fluoro-4-nitroanisole with n-hexylamine, a related compound, shows evidence of substitution reactions that involve different triplet excited states, indicating complex reaction pathways that could also be relevant to 3-Fluoro-4-methoxyaniline.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3-Fluoro-4-methoxyaniline, such as melting point, boiling point, solubility, and stability, are not explicitly detailed in the provided papers. However, the presence of the fluorine atom is known to affect the chemical shift in NMR spectroscopy due to its electronegativity, and this could be used to analyze the compound's structure. Additionally, the methoxy group could confer increased solubility in organic solvents compared to the parent aniline compound.

Scientific Research Applications

• Synthesis of Complex Organic Compounds

  • 3-Fluoro-4-methoxyaniline is used in the synthesis of diverse organic compounds. For example, it plays a crucial role in Ullmann methoxylation, facilitating the preparation of compounds like 2-Fluoro-4-Methoxyaniline, which are significant in the field of organic synthesis (Ragan et al., 2003).

• Imaging Agent for Viral Infection and Gene Therapy

  • This compound has been investigated for its potential as an imaging agent in PET (Positron Emission Tomography). Specifically, derivatives of 3-Fluoro-4-methoxyaniline, such as [18F]FHBG, show promise for imaging viral infections or transfected cells in gene therapy (Alauddin & Conti, 1998).

• Synthesis of Fluorinated Heterocyclic Compounds

  • It's utilized in the creation of fluorinated heterocyclic compounds. Research has shown its application in synthesizing pyrazolones, pyrimidines, coumarines, and benzothiopyranones, highlighting its versatility in chemical synthesis (Shi, Wang, & Schlosser, 1996).

• Wastewater Treatment

  • In environmental science, 3-Fluoro-4-methoxyaniline derivatives are explored for treating wastewater containing toxic chemicals, especially in the dye and pharmaceutical industries. Studies on Fenton-like oxidation processes have involved methoxyanilines, demonstrating their relevance in environmental remediation (Chaturvedi & Katoch, 2020).

• Synthesis of Biologically Active Compounds

  • It is used in the synthesis of biologically active compounds, such as anti-tyrosinase and anti-melanogenic agents, which are important in dermatology and cosmetic science. Derivatives like N-(4-fluorobenzyl)-3-fluoro-4-methoxyaniline have shown significant activity in inhibiting skin hyperpigmentation (Singpanna et al., 2022).

• Innovations in Polymer Science

  • Research has explored its application in polymer science, particularly in synthesizing soluble conducting polymers. The ortho-methoxyaniline polymer, closely related to 3-Fluoro-4-methoxyaniline, exhibits promising characteristics for industrial applications (Macinnes & Funt, 1988).

Safety And Hazards

3-Fluoro-4-methoxyaniline may cause damage to organs through prolonged or repeated exposure. It may cause respiratory irritation and is harmful if inhaled. It is toxic if inhaled, causes serious eye irritation, and causes skin irritation. It is harmful in contact with skin and is harmful if swallowed.

Future Directions

The future directions of 3-Fluoro-4-methoxyaniline are not explicitly mentioned in the search results.

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