84478-87-5 | 2-BROMO-4-FLUORO-5-NITROPHENOL

CAS:84478-87-5 | 2-BROMO-4-FLUORO-5-NITROPHENOL,Description

2-Bromo-4-fluoro-5-nitrophenol is a compound that has been synthesized and studied for various properties and potential applications. The compound is characterized by the presence of bromo, fluoro, and nitro substituents on the phenol ring, which significantly influence its chemical behavior and interactions.

Synthesis Analysis

The synthesis of 2-Bromo-4-fluoro-5-nitrophenol has been reported using 2-methoxy-5-nitroaniline as a starting material. The process involves a diazotization reaction followed by the Sandmeyer reaction to yield 2-bromo-4-nitroanisole, which is then treated with sodium hydroxide to undergo a nucleophilic substitution reaction. The final product is obtained after acidification with hydrochloric acid, with a reported yield of 55.8%. The synthesis pathway is considered simple, efficient, and suitable for commercial production.

Molecular Structure Analysis

The molecular structure of related compounds has been elucidated using various spectroscopic techniques such as FT-IR, UV-Vis, NMR, and single-crystal X-ray diffraction methods. Density Functional Theory (DFT) calculations have been employed to optimize the geometry and investigate the electronic properties of similar bromo-fluoro-nitrophenol derivatives. These studies provide insights into the intramolecular interactions and the electronic distribution within the molecule, which are crucial for understanding the reactivity and potential applications of 2-Bromo-4-fluoro-5-nitrophenol.

Chemical Reactions Analysis

The presence of bromo and nitro groups on the phenol ring makes the compound a candidate for further chemical transformations, such as nucleophilic aromatic substitution reactions. These reactions can lead to the formation of various derivatives and complexes, which can be of interest in fields such as medicinal chemistry and materials science.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-Bromo-4-fluoro-5-nitrophenol and its derivatives are influenced by the substituents on the phenol ring. The strong electron-withdrawing effects of the nitro group, combined with the electron-withdrawing and donating effects of the fluoro and bromo groups, respectively, affect the acidity of the phenolic hydrogen and the overall stability of the molecule. The solvent effects on complexation reactions involving similar compounds have been studied, indicating that solvent polarity can significantly affect the outcome of such reactions. Additionally, computational studies have provided information on the polarizability, hyperpolarizability, and molecular electrostatic potential of related compounds, which are important for understanding their reactivity and interactions with other molecules.

Scientific Research Applications

Chemical Reactions and Synthesis

• Nitration of halophenols like p-chloro-, p-fluoro-, and p-bromo-phenol leads to the formation of 4-halo-4-nitrocyclohexa-2, 5-dienones along with halo-nitrophenols. These compounds, including derivatives of 2-Bromo-4-fluoro-5-nitrophenol, undergo isomerization at certain temperatures (Clewley et al., 1989).
• 2-Bromo-4-nitrophenol, closely related to 2-Bromo-4-fluoro-5-nitrophenol, can be synthesized using 2-methoxy-5-nitroaniline through diazotization and the Sandmeyer reaction. This synthesis pathway is suitable for commercial production (Li Zi-ying, 2008).

Analytical Chemistry and Detection

• Gas chromatography has been used to separate isomers of nitro-, fluoro-, bromo-, and iodophenols, including compounds similar to 2-Bromo-4-fluoro-5-nitrophenol (Ma & Spiegel, 1966).
• In the study of fluorescent detection, 2-Bromo-4-fluoro-5-nitrophenol or its derivatives could potentially be used in the detection of nitroaromatic compounds like TNT and 4-nitrophenol, as demonstrated by the use of bovine serum albumin functionalized fluorescent gold nanoclusters (Yang et al., 2014).

Biological and Environmental Studies

• 2-Bromo-4-fluoro-5-nitrophenol may have potential applications in biological studies, as seen in the use of 2-Fluoro-4-nitrophenol-β-D-galactopyranoside for imaging beta-galactosidase activity, which is relevant for gene-reporter molecule studies in biomedical research (Kodibagkar et al., 2006).

Catalysis and Chemical Reactions

• The compound's structural analogues, like 4-nitrophenol, have been investigated for their catalytic reduction using gold nanoparticles, suggesting potential applications of 2-Bromo-4-fluoro-5-nitrophenol in catalysis (Thawarkar et al., 2018).

Molecular Interactions and Properties

• The structural, spectroscopic, and electronic properties of compounds structurally similar to 2-Bromo-4-fluoro-5-nitrophenol have been extensively studied to understand their molecular interactions (Bozkurt et al., 2019).

Safety And Hazards

2-Bromo-4-fluoro-5-nitrophenol is classified as a dangerous substance. It can cause serious eye irritation and may be harmful if inhaled. Precautionary measures include avoiding dust formation, avoiding contact with skin and eyes, and using personal protective equipment.

Future Directions

The global 2-Bromo-4-fluoro-5-nitrophenol market has been rapidly expanding in recent times and is expected to register a robust revenue CAGR over the forecast period.

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