401-80-9 | 3-Fluorobenzotrifluoride

CAS:401-80-9 | 3-Fluorobenzotrifluoride,Description

Synthesis Analysis

The synthesis of fluoro-substituted aromatic hydrocarbons, such as 3-fluorobenzotrifluoride derivatives, is a topic of interest due to their utility in studying the mechanistic details of metabolic processes involving cytochrome P450. In one study, the synthesis of 3-fluorobenzo[a]pyrene (3-FBP) was achieved through a five-step process starting from 6-chlorobenzo[a]pyrene (6-ClBP), with an overall yield of 16% for both 1-FBP and 3-FBP. This process involved nitration, reduction, diazotization, and heating in toluene to obtain the desired fluorinated compounds.

Molecular Structure Analysis

The molecular structure of 3-fluorobenzotrifluoride derivatives can exhibit complex behavior, as evidenced by the solvatomorphism observed in 3-Fluorobenzoylaminophenyl 3-fluorobenzoate. This compound crystallizes in dimorphic forms, with the crystalline structure being influenced by a combination of strong N−H···O hydrogen bonds and weaker interactions, including C−H···O, C−H···F, and aromatic π···π stacking interactions. The extent of disorder associated with the fluorine atoms varies between the two forms, highlighting the subtle interplay of intermolecular forces.

Chemical Reactions Analysis

The reactivity of 3-fluorobenzotrifluoride derivatives can be explored through the synthesis of related compounds. For instance, 1-(4-Fluorobenzoyl)-3-(isomeric fluorophenyl)thioureas were prepared by reacting 4-fluorobenzoyl isothiocyanate with isomeric fluoroanilines. The resulting compounds were characterized by various spectroscopic techniques, and their crystal packing was analyzed, revealing centrosymmetric dimers formed through intermolecular N−H···S=C hydrogen bonds.

Physical and Chemical Properties Analysis

Vibrational spectroscopy, including FT-Raman and Fourier transform infrared spectroscopy, has been used to investigate the structure of 3-aminobenzotrifluoride, a related compound to 3-fluorobenzotrifluoride. Theoretical calculations using ab initio and density functional theory complemented the experimental data, providing insights into the equilibrium geometry, vibrational frequencies, and thermodynamic functions of the compound. This comprehensive analysis aids in understanding the physical and chemical properties of such fluorinated aromatic compounds.

Case Studies

While the provided data does not include specific case studies, the synthesis and analysis of 3-fluorobenzotrifluoride derivatives have implications for various fields, including medicinal chemistry and environmental science. For example, the synthesis of 4-fluorobenzo[b][1,6]naphthyridines and 4-fluoroisoquinolines via iminofluorination of alkynes demonstrates the potential for creating complex fluorinated molecules that could serve as pharmaceutical intermediates or probes for biological systems.

Scientific Research Applications

• Fluoroform as a Difluorocarbene Source : Fluoroform (CHF3) can be used as a source of difluorocarbene for converting phenols and thiophenols into difluoromethoxy and difluorothiomethoxy derivatives. This method utilizes moderate temperatures and atmospheric pressure, providing moderate to good yields (Thomoson & Dolbier, 2013).
• Continuous-Flow Synthesis : The continuous-flow synthesis of 5-fluoro-2-nitrobenzotrifluoride is achieved through the nitration of 3-fluorobenzotrifluoride. This process is safer and more efficient than traditional methods, thanks to enhanced mass and heat transfer rates (Chen et al., 2020).
• Electrochemistry of Ionic Liquids : The electrochemistry of 1-Butyl-3-methyl-1H-imidazolium Tetrafluoroborate ionic liquid was studied, revealing the production of BF3 and fluorocarbons at the anode while undergoing dimerization and dealkylation reactions at the cathode (Xiao & Johnson, 2003).
• Catalytic Fluoromethylation : Photoredox catalysis has emerged as a useful tool for radical reactions, including catalytic fluoromethylation of carbon-carbon multiple bonds. This method offers efficient and selective radical fluoromethylation under mild conditions (Koike & Akita, 2016).
• Transition Metal Fluoride Complexes in Catalysis : Molecular iron(II) fluorides have potential applications in catalysis, including C-F bond activation and fluorocarbon functionalization, demonstrating the versatility of transition metal fluoride complexes (Vela et al., 2005).
• Synthesis of Novel Herbicides : The synthesis process of novel herbicides like Beflubutamid involves the nitrification reaction of 2-fluorobenzotrifluoride, showcasing its role in the development of agricultural chemicals (Chen Huan-you, 2012).
• Magnetic Sorbents in Environmental Analysis : The synthesis of 3-fluorobenzoyl chloride functionalized magnetic nanoparticles for the efficient extraction of perfluorinated compounds from river water samples highlights its application in environmental analysis (Yan et al., 2013).

Safety And Hazards

3-Fluorobenzotrifluoride is highly flammable and can cause skin and eye irritation. It may also cause respiratory irritation. Precautionary measures include avoiding breathing its vapors, mist, or gas, ensuring adequate ventilation, and keeping away from heat, sparks, open flames, and hot surfaces.

Relevant Papers

One relevant paper found discusses the synthesis of 5-fluoro-2-nitrobenzotrifluoride in a continuous-flow millireactor system through the nitration of 3-fluorobenzotrifluoride.

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