50824-05-0 | 4-(Trifluoromethoxy)benzyl bromide

CAS:50824-05-0 | 4-(Trifluoromethoxy)benzyl bromide ,Description

4-(Trifluoromethoxy)benzyl bromide (TFMB) is a trifluoromethylated organic compound that has been studied for its potential applications in various fields of science. It is a colorless liquid with a boiling point of 121°C and a molar mass of 197.01 g/mol. TFMB is a versatile reagent that has been used in a variety of synthetic reactions, such as alkylation and substitution reactions, as well as in the synthesis of pharmaceuticals and agrochemicals. In addition, TFMB has been studied for its potential applications in the fields of biochemistry and physiology, as well as for its ability to facilitate the synthesis of new drugs and other compounds.
 

Scientific Research Applications

• Generation of Arynes and Their Applications:
  • Treatment of 1-bromo-2-(trifluoromethoxy)benzene with lithium diisopropylamide (LDA) at low temperatures generates phenyllithium intermediates. These intermediates can be further reacted to produce various compounds, including 1- and 2-(trifluoromethoxy)naphthalenes. This process demonstrates the application of trifluoromethoxy benzyl bromides in generating arynes for organic synthesis (Schlosser & Castagnetti, 2001).
• Trifluoromethoxylation of Aliphatic Substrates:
  • The trifluoromethoxide anion, generated under specific conditions, can substitute activated bromides, including benzyl bromide, to form aliphatic trifluoromethyl ethers. This indicates the use of trifluoromethoxy benzyl bromides in introducing trifluoromethoxy groups into aliphatic compounds (Marrec et al., 2010).
• Electrochemical Studies and Grafting:
  • Benzyl bromides, including 4-nitrobenzyl bromide, can undergo electrochemical reductions at solid electrodes. This process is used for generating free radicals which can couple or add onto cathodic materials, showcasing another application in organic synthesis and materials science (Jouikov & Simonet, 2010).
• Preparation of Polymers with Controlled Molecular Architecture:
  • In the synthesis of dendritic macromolecules, 4-(trifluoromethoxy)benzyl bromide can be used as an intermediate for coupling with polyfunctional cores. This highlights its role in the field of polymer chemistry (Hawker & Fréchet, 1990).
• Carbene-Catalyzed Reductive Coupling:
  • The generation of benzyl radicals from benzyl bromides, including nitrobenzyl bromides, via N-heterocyclic carbene (NHC) catalysis under reductive conditions, is another application. This showcases its use in radical reactions and organic synthesis (Li et al., 2016).
• Study of Electron-Withdrawing Substituent Effects:
  • Research on the electron-withdrawing effects of the trifluoromethoxy group compared to other groups, like methoxy and trifluoromethyl, has used 4-(trifluoromethoxy)benzyl bromide as a case study. This is significant in understanding the chemical properties and reactivity of such compounds (Castagnetti & Schlosser, 2002).
• Chemoselective Trifluoromethylation:
  • The compound has been used in copper-mediated chemoselective trifluoromethylation at the benzylic position, showing its utility in introducing trifluoromethyl groups into benzyl bromides. This method is useful for creating structural diversity in medicinal chemistry (Kawai et al., 2011).

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