886762-75-0 | 4-BROMO-3-FLUORO-2-NITROANILINE

CAS:886762-75-0 | 4-BROMO-3-FLUORO-2-NITROANILINE,Description

4-Bromo-3-fluoro-2-nitroaniline is a compound that is not directly mentioned in the provided papers, but its structural analogs and related compounds have been studied extensively. These compounds are typically intermediates in the synthesis of various dyes, pharmaceuticals, and other biologically active compounds. The presence of bromo, fluoro, and nitro substituents on the aromatic ring can significantly affect the chemical reactivity and physical properties of these molecules.

Synthesis Analysis

The synthesis of related compounds such as 2,6-dibromo-4-nitroanilineand 4-bromo-2-fluorobiphenylinvolves halogenation and nitration reactions. For instance, 2,6-dibromo-4-nitroaniline is prepared from 4-nitroaniline using bromide–bromate salts in an aqueous acidic medium. Similarly, 4-bromo-2-fluorobiphenyl is synthesized through diazotization and coupling reactions, or by bromination of 2-fluoroaniline followed by a cross-coupling reaction. These methods highlight the importance of careful control of reaction conditions to achieve the desired substitution pattern on the aromatic ring.

Molecular Structure Analysis

The molecular structure and properties of compounds similar to 4-Bromo-3-fluoro-2-nitroaniline have been characterized using various spectroscopic techniques. For example, a Schiff-base compound with a similar substitution pattern was investigated using FT-IR, UV-Vis, NMR, and single-crystal X-ray diffraction methods. Theoretical calculations such as DFT were also employed to predict the molecular geometry, vibrational frequencies, and electronic properties. These studies provide insights into the electronic distribution and stability of the molecule, which are crucial for understanding its reactivity.

Chemical Reactions Analysis

The reactivity of bromo- and fluoro-substituted nitroaromatic compounds has been explored in various chemical reactions. For instance, 3-bromo-2-nitrobenzo[b]thiophene undergoes aromatic nucleophilic substitution with amines, leading to unexpected rearrangements. Similarly, nitrosation of 2-aryl-1-bromo-1-fluorocyclopropanes has been studied as an approach to synthesize isoxazolines, demonstrating the influence of halogen substituents on reaction pathways. These studies suggest that 4-Bromo-3-fluoro-2-nitroaniline would also exhibit interesting reactivity, potentially useful in the synthesis of heterocyclic compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated nitroaromatic compounds are influenced by the nature and position of the substituents. The presence of electron-withdrawing groups such as nitro, bromo, and fluoro can affect the acidity, boiling point, solubility, and stability of the compound. For example, the synthesis of 1-(4-bromo-2-fluorophenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one involves multiple steps, including nitration, chlorination, and condensation, which are sensitive to the substituents' electronic effects. The optimization of reaction conditions, as seen in the synthesis of 4-bromo-2-fluorobiphenyl, can lead to significant cost savings and improved yields, highlighting the importance of understanding these properties for practical applications.

Scientific Research Applications

• Organic Chemistry

  • Application : 4-Bromo-3-fluoro-2-nitroaniline is a valuable compound that can be applied throughout organic chemistry. It’s also known as 6-amino-3-bromo-2-fluoronitrobenzene.
  • Methods of Application : This halogenated aniline is used as a building block to prepare larger scaffolds with biological relevance. The specific methods of application or experimental procedures would depend on the particular synthesis being performed.
  • Results or Outcomes : The outcomes of using 4-Bromo-3-fluoro-2-nitroaniline as a building block would vary depending on the specific synthesis. It’s generally used to create compounds with biological relevance, which could be utilized in the pharmaceutical industry.

• Biochemistry

  • Application : It has been used in the reduction of nitro-aromatic compounds and the oxidation of alcohols.
  • Methods of Application : The compound is used as a reagent for synthetic transformations. The specific methods of application or experimental procedures would depend on the particular reaction being performed.
  • Results or Outcomes : The outcomes of using 4-Bromo-3-fluoro-2-nitroaniline in these reactions would depend on the specific reaction. It’s generally used to facilitate the reduction of nitro-aromatic compounds and the oxidation of alcohols.

• Hair Dye Manufacturing

  • Application : 4-Fluoro-3-nitroaniline, a compound similar to 4-Bromo-3-fluoro-2-nitroaniline, is used in the preparation of commercial hair dyes.
  • Results or Outcomes : The outcomes of using 4-Fluoro-3-nitroaniline in hair dye manufacturing would depend on the specific hair dye formulation. It’s generally used to create a variety of color options for consumers.

• Antibiotic Synthesis

  • Application : A precursor to the antibiotic candidate TBI-233 is synthesized from 2-fluoro-4-nitroaniline, a compound similar to 4-Bromo-3-fluoro-2-nitroaniline.
  • Results or Outcomes : The outcomes of using 2-fluoro-4-nitroaniline in antibiotic synthesis would depend on the specific synthesis. It’s generally used to create potential antibiotic candidates.

• Nanotechnology

  • Application : 2-Fluoro-4-nitroaniline has been used to introduce sp3 defects onto semiconducting single-walled carbon nanotubes (SWCNTs) for organic color center-tailored carbon nanotubes.
  • Results or Outcomes : The outcomes of using 2-fluoro-4-nitroaniline in nanotechnology would depend on the specific experiment. It’s generally used to tailor the properties of carbon nanotubes.
• Pharmaceuticals
  • Application : 4-Bromo-3-fluoro-2-nitroaniline is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals.
  • Results or Outcomes : The outcomes of using 4-Bromo-3-fluoro-2-nitroaniline in pharmaceutical synthesis would depend on the specific synthesis. It’s generally used to create potential pharmaceutical candidates.

Also, it’s important to note that while 4-Bromo-3-fluoro-2-nitroaniline has these applications, its similar compounds like 4-Fluoro-3-nitroaniline and 2-Fluoro-4-nitroaniline also have various applications in fields like hair dye manufacturing, antibiotic synthesis, and nanotechnology.

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