403-19-0 | 2-Fluoro-4-nitrophenol

CAS:403-19-0 | 2-Fluoro-4-nitrophenol,Description

2-Fluoro-4-nitrophenol is an important chemical intermediate with applications in various fields of chemistry and material science. Its synthesis, structure, and properties have been studied to understand its reactivity and utility in chemical syntheses and applications.

Synthesis Analysis

2-Fluoro-4-nitrophenol can be synthesized through various methods. For instance, Lu Zhou (2008) describes a four-step synthesis from m-fluoroaniline, involving diazotization, hydrolysis, nitration, and isomer separation, yielding a final product with 99.6% purity (Zhou, 2008). Another method involves methoxylation and demethylation of 2,4-difluoronitrobenzene, as detailed by Zhang Zhi-de (2011), achieving a 38.7% yield and 99.5% purity (Zhi-de, 2011).

Molecular Structure Analysis

The molecular structure of 2-Fluoro-4-nitrophenol has been characterized using various spectroscopic techniques, including FT-IR, UV-Vis, NMR, and X-ray crystallography. A study by İ. Bozkurt et al. (2019) used DFT and Time-Dependent DFT methods to investigate its molecular geometry, vibrational frequencies, and electronic properties, offering insights into its structural characteristics and stability (Bozkurt et al., 2019).

Chemical Reactions and Properties

2-Fluoro-4-nitrophenol participates in a variety of chemical reactions due to its reactive functional groups. Its electrophilic and nucleophilic properties facilitate its use in synthesizing heterocyclic compounds and polymers. For example, Soňa Křupková et al. (2013) explored its use as a multireactive building block for synthesizing nitrogenous heterocycles (Křupková et al., 2013) .

Physical Properties Analysis

The physical properties of 2-Fluoro-4-nitrophenol, such as melting point, solubility, and density, are crucial for its application in chemical synthesis. These properties are determined by its molecular structure and can influence its behavior in chemical reactions.

Chemical Properties Analysis

2-Fluoro-4-nitrophenol's chemical properties, including acidity, basicity, and reactivity towards various reagents, are defined by its functional groups. Its nitro and fluoro groups make it a versatile intermediate for further chemical modifications and syntheses. Studies like those by Ekaeva et al. (1995) have explored its reactivity in Baeyer-Villiger oxidations, showcasing its utility in synthesizing fluorophenols (Ekaeva et al., 1995).

Scientific Research Applications

• Chemical Synthesis

  • 2-Fluoro-4-nitrophenol is often used as a building block in chemical synthesis. The specific reactions it’s involved in can vary widely depending on the desired end product.

• Derivative of m-fluoronitrobenzene

  • This compound is a derivative of m-fluoronitrobenzene. It’s used in reactions that require a fluorine atom and a nitro group on the phenol ring.

• Crystal Structure Studies

  • The crystal structure of a complex of α-cyclodextrin with 2-fluoro-4-nitrophenol has been studied using X-ray diffraction techniques. This helps scientists understand how the compound interacts with other molecules at the atomic level.

• Preparation of Fluoroanilines

  • 4-Fluoro-2-nitrophenol may be used in the preparation of 5-fluoro-2-methoxyaniline and 5-fluoro-2-hydroxyaniline. These compounds are useful in the synthesis of various pharmaceuticals and dyes.

• Preparation of Fluorinated Compounds

  • 2-Fluoro-4-nitrophenol can be used in the preparation of other fluorinated compounds. Fluorinated compounds have a wide range of applications, including in pharmaceuticals, agrochemicals, and materials science.

• Nitration of Fluorophenols

  • This compound can be formed during the nitration of 4-fluorophenol. The nitration process is important in the production of various dyes, pharmaceuticals, and explosives.

Safety And Hazards

2-Fluoro-4-nitrophenol is toxic if swallowed. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation. Safety measures include avoiding breathing dust/fume/gas/mist/vapors/spray, wearing protective gloves/clothing/eye protection/face protection, and using only outdoors or in a well-ventilated area.

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