402-44-8 | 4-Fluorobenzotrifluoride

CAS:402-44-8 | 4-Fluorobenzotrifluoride,Description

4-Fluorobenzotrifluoride is a halogenated benzotrifluoride derivative¹. It is a clear colorless to light yellow liquid4-Fluorobenzotrifluoride is a halogenated benzotrifluoride derivative1" h="ID=SERP,5015.1">².

Synthesis Analysis

4-Fluorobenzotrifluoride has been used in the synthesis of 2,2’-bis (trifluoromethylphenoxy)biphenyl via nucleophilic aromatic substitution reaction with 2,2’-biphenol, (S)-fluoxetine, potent inhibitor of neuronal serotonin-uptake and 1-aryloxy-2-substituted aminomethyltetrahydronaphthalene derivatives³⁴.
 

Molecular Structure Analysis

The molecular formula of 4-Fluorobenzotrifluoride is C7H4F4⁵. The InChIKey is UNNNAIWPDLRVRN-UHFFFAOYSA-NThe molecular formula of 4-Fluorobenzotrifluoride is C7H4F45" h="ID=SERP,5015.1">⁵. The Canonical SMILES is C1=CC(=CC=C1C(F)(F)F)F⁵.
 

Chemical Reactions Analysis

4-Fluorobenzotrifluoride undergoes a nucleophilic aromatic substitution reaction with 2,2’-biphenol, (S)-fluoxetine, potent inhibitor of neuronal serotonin-uptake and 1-aryloxy-2-substituted aminomethyltetrahydronaphthalene derivatives⁴².
 

Physical And Chemical Properties Analysis

4-Fluorobenzotrifluoride has a molecular weight of 164.10 g/mol⁵. It is slightly soluble in water4-Fluorobenzotrifluoride has a molecular weight of 164.10 g/mol5" h="ID=SERP,5015.1">⁷. The density is 1.293g/mL at 25°C (lit.)⁷.
 

Scientific Research Applications

Application 1: Microbial Defluorination

• Scientific Field : Environmental Microbiology
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the study of microbial defluorination, specifically the capacity of microbes to defluorinate polyfluorinated organic compounds. This is important for maintaining the environment as many organofluorine chemicals are considered to be persistent and toxic environmental pollutants.
• Methods of Application or Experimental Procedures : A low-volume, high-throughput screening method is used to determine the defluorination capacity of microbes and their enzymes. The method is based on selective binding of fluoride to a lanthanum chelate complex that gives a purple-colored product. It was miniaturized to determine biodefluorination in 96-well microtiter plates by visual inspection or robotic handling and spectrophotometry. The products extracted from incubation of E. coli pDTG 602 with 4-fluorobenzotrifluoride were analyzed.
• Results or Outcomes : The method revealed 21 new compounds undergoing defluorination. A compound with four fluorine substituents, 4-fluorobenzotrifluoride, was shown to undergo defluorination to the greatest extent. The mechanism of its defluorination was studied to reveal a latent microbial propensity to defluorinate trifluoromethylphenyl groups, a moiety that is commonly incorporated into numerous pharmaceutical and agricultural chemicals.

Application 2: Synthesis of Biphenyl Compounds

• Scientific Field : Organic Chemistry 
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the synthesis of 2,2’-bis(trifluoromethylphenoxy)biphenyl . This compound is a key intermediate in the production of various organic compounds.
• Methods of Application or Experimental Procedures : The synthesis involves a nucleophilic aromatic substitution reaction with 2,2’-biphenol . The reaction conditions typically involve heating the reactants in a suitable solvent.
• Results or Outcomes : The reaction results in the formation of 2,2’-bis(trifluoromethylphenoxy)biphenyl. .

Application 3: Synthesis of Fluoxetine

• Scientific Field : Pharmaceutical Chemistry 
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the synthesis of (S)-fluoxetine , a potent inhibitor of neuronal serotonin-uptake. This is a key step in the production of fluoxetine, a widely used antidepressant.
• Methods of Application or Experimental Procedures : The synthesis involves a series of reactions, including nucleophilic aromatic substitution. The specific reaction conditions can vary depending on the desired product.
• Results or Outcomes : The reaction results in the formation of (S)-fluoxetine. .

Application 4: Synthesis of Aminomethyltetrahydronaphthalene Derivatives

• Scientific Field : Organic Chemistry 
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the synthesis of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalene derivatives . These compounds have potential applications in various fields, including materials science and pharmaceuticals.
• Methods of Application or Experimental Procedures : The synthesis involves a series of reactions, including nucleophilic aromatic substitution. The specific reaction conditions can vary depending on the desired product.
• Results or Outcomes : The reaction results in the formation of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalene derivatives. .

Application 5: Synthesis of Fluorinated Epoxy Resins

• Scientific Field : Polymer Chemistry 
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the synthesis of fluorinated epoxy resins . These resins have improved thermal stability and chemical resistance compared to non-fluorinated resins.
• Methods of Application or Experimental Procedures : The synthesis involves a series of reactions, including nucleophilic aromatic substitution. The specific reaction conditions can vary depending on the desired product.
• Results or Outcomes : The reaction results in the formation of fluorinated epoxy resins. .

Application 6: Synthesis of Fluorinated Liquid Crystals

• Scientific Field : Materials Science 
• Summary of the Application : 4-Fluorobenzotrifluoride is used in the synthesis of fluorinated liquid crystals . These materials have potential applications in display technologies.
• Methods of Application or Experimental Procedures : The synthesis involves a series of reactions, including nucleophilic aromatic substitution. The specific reaction conditions can vary depending on the desired product.
• Results or Outcomes : The reaction results in the formation of fluorinated liquid crystals. .

Safety And Hazards

4-Fluorobenzotrifluoride is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It can cause skin irritation, serious eye irritation, and may cause respiratory irritation⁸.

Future Directions

There is a growing interest in the ability to screen many natural and engineered microbes against large numbers of fluorinated compounds simultaneously⁶. This could lead to new discoveries in the defluorination capacity of microbes and their enzymesThere is a growing interest in the ability to screen many natural and engineered microbes against large numbers of fluorinated compounds simultaneously6" h="ID=SERP,5015.1">⁶.

Please note that this information is based on the available resources and might not include all the aspects of 4-Fluorobenzotrifluoride.

More Information