50824-04-9 | 4-Bromo-2-(trifluoromethyl)phenol

CAS:50824-04-9 | 4-Bromo-2-(trifluoromethyl)phenol,Description

Synthesis Analysis

The synthesis of 4-Bromo-2-(trifluoromethyl)phenol and its derivatives involves various chemical reactions, highlighting the versatility of this compound as a precursor. For instance, it has been synthesized through reactions involving bromosalicylaldehyde with aminopyridine, showcasing the compound's role in forming Schiff base compounds (Khalaji et al., 2017). Another example includes its synthesis from 4-methylphenol by oxidative bromination, emphasizing efficient production methods with high yields (Ren Qun-xiang, 2004).

Molecular Structure Analysis

The molecular structure of 4-Bromo-2-(trifluoromethyl)phenol derivatives has been extensively studied using various techniques, including X-ray diffraction, NMR spectroscopy, and DFT calculations. These studies reveal the compound's crystalline structure, molecular geometry, and intramolecular interactions, such as hydrogen bonding, which play a crucial role in stabilizing the molecular conformation (Khalaji et al., 2017).

Chemical Reactions and Properties

4-Bromo-2-(trifluoromethyl)phenol participates in various chemical reactions, including electrophilic aromatic substitution and coupling reactions. These reactions are fundamental in the synthesis of complex organic molecules, demonstrating the compound's reactivity and versatility. For example, it undergoes bromination and isomerization reactions under specific conditions, leading to the formation of bromophenols and bromodienones (Fischer & Henderson, 1983).

Physical Properties Analysis

The physical properties of 4-Bromo-2-(trifluoromethyl)phenol, such as solubility, melting point, and boiling point, are crucial for its handling and application in chemical synthesis. These properties are determined by the compound's molecular structure and intermolecular forces.

Chemical Properties Analysis

The chemical properties, including acidity, basicity, and reactivity towards different reagents, are essential for understanding the compound's behavior in various chemical environments. Its role as a precursor in synthesizing Schiff base compounds highlights its reactivity and usefulness in organic synthesis (Khalaji et al., 2017).

Scientific Research Applications

• Pharmaceuticals and Agrochemicals

  • 4-Bromo-2-(trifluoromethyl)phenol is a basic building block for numerous pharmaceutical drugs.
  • It’s also used in the synthesis of trifluoromethylpyridines, which are key structural motifs in active agrochemical and pharmaceutical ingredients.
  • The major use of trifluoromethylpyridine (TFMP) derivatives is in the protection of crops from pests.
  • More than 20 new TFMP-containing agrochemicals have acquired ISO common names.
  • Several TFMP derivatives are also used in the pharmaceutical and veterinary industries.
  • Five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval.
  • Many candidates are currently undergoing clinical trials.

• Laboratory Chemicals

  • 4-Bromo-2-(trifluoromethyl)phenol is used as a laboratory chemical.

Safety And Hazards

4-Bromo-2-(trifluoromethyl)phenol may cause skin irritation, serious eye irritation, and respiratory irritation. It’s recommended to avoid breathing its dust/fume/gas/mist/vapors/spray and to use it only outdoors or in a well-ventilated area.

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