184970-25-0 | 2-FLUORO-3-(TRIFLUOROMETHYL)BENZYL BROMIDE

CAS:184970-25-0 | 2-FLUORO-3-(TRIFLUOROMETHYL)BENZYL BROMIDE,Description

Synthesis Analysis

The synthesis of fluorinated compounds often involves the selective introduction of fluorine or trifluoromethyl groups into specific positions of aromatic or heteroaromatic rings. A recent advancement includes the use of fluoroform-derived CuCF3, demonstrating high reactivity towards aryl and heteroaryl halides. This method facilitates the trifluoromethylation of a broad variety of iodoarenes and some aromatic bromides, including pyridine and pyrimidine derivatives, achieving nearly quantitative yield in certain cases (Lishchynskyi et al., 2013).

Molecular Structure Analysis

The molecular structure of fluorinated compounds, including 2-Fluoro-3-(trifluoromethyl)benzyl bromide, is characterized by the presence of fluorine atoms, which significantly influence the compound's physical and chemical properties. The crystal structures of related N-[2-(trifluoromethyl)phenyl]benzamides have been reported, showcasing the impact of fluorine atoms on the dihedral angles between benzene rings (Suchetan et al., 2016).

Chemical Reactions and Properties

Fluorinated compounds are known for their unique reactivity due to the electron-withdrawing nature of fluorine, which makes them valuable intermediates in organic synthesis. The trifluoromethylation of aryl and heteroaryl halides using fluoroform-derived CuCF3 is a notable reaction, allowing for the introduction of trifluoromethyl groups into various molecular frameworks with high chemoselectivity and yield. This process demonstrates the utility of fluorinated compounds in synthesizing benzotrifluorides and other fluorinated derivatives (Lishchynskyi et al., 2013).

Scientific Research Applications

• Drug Design and Medicinal Chemistry : The introduction of fluorinated moieties like the trifluoromethyl group in organic molecules can lead to significant changes in biological activities, making this strategy widely used in drug design (Zhao & Hu, 2012).
• Organic Synthesis : The synthesis of α-fluoro-α-(trifluoromethyl)-β-amino esters via zinc-mediated coupling reaction of benzyl 2-bromo-2,3,3,3-tetrafluoropropanoate with chiral imines has been demonstrated, highlighting the utility of fluorinated compounds in organic synthesis (Sekiguchi et al., 2004).
• Materials Science : The photoredox/nickel dual catalytic system used for cross-coupling of benzylic α-trifluoromethylated alkylboron reagents with (hetero)aryl bromides, avoiding harsh conditions and high temperatures, exemplifies the application in materials science (Ryu et al., 2016).
• Chemical Reactivity and Synthesis : The trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3, performing well in the absence of extra ligands, indicates its potential in various chemical synthesis processes (Lishchynskyi et al., 2013).
• Pharmaceutical Applications : The synthesis of [F-18]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC), a tumor-avid amino acid for positron emission tomography, highlights the compound's relevance in pharmaceutical applications (Shoup & Goodman, 1999).
• Catalysis and Synthesis Techniques : The copper-mediated chemoselective trifluoromethylation of benzyl bromides using shelf-stable electrophilic trifluoromethylating reagents under mild conditions is another significant application in catalysis and synthesis (Kawai et al., 2011).
• Analytical Chemistry : In analytical chemistry, the study of the crystal structures of various N-[2-(trifluoromethyl)phenyl]benzamides demonstrates the application of these compounds in elucidating structural properties of molecules (Suchetan et al., 2016).

Safety And Hazards

“2-Fluoro-3-(trifluoromethyl)benzyl bromide” is considered hazardous. It can cause severe skin burns and eye damage, and may cause respiratory irritation. The compound should be handled with protective gloves, clothing, and eye/face protection. It should be used only outdoors or in a well-ventilated area.

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