3796-23-4 | 3-Trifluoromethylpyridine

CAS:3796-23-4 | 3-Trifluoromethylpyridine,Description

3-(Trifluoromethyl)pyridine is a pyridine derivative significant in various chemical syntheses and reactions. Its unique structure and properties make it a valuable compound in organic chemistry.

Synthesis Analysis

• A novel synthesis strategy for poly-substituted 3-trifluoromethyl pyridines involves C-F bond breaking of the anionically activated fluoroalkyl group, providing high yields under metal-free conditions (Chen et al., 2010).
• The Hetero-Diels—Alder Reaction of 3-(Trifluoroacetyl)chromones with cyclic enol ethers leads to the synthesis of 3-aroyl-2-(trifluoromethyl)pyridines (Sosnovskikh et al., 2007) .
• The synthesis of 2,3-Dichloro-5-trifluoromethyl pyridine, a key pyridine derivative, is used in pesticide synthesis (Lu Xin-xin, 2006).

Molecular Structure Analysis

• X-ray diffraction analysis helps establish the structure of synthesized pyridines, revealing their molecular geometry and bonding (Sosnovskikh et al., 2007) .
• The molecular and crystal structures of various pyridine derivatives have been studied, contributing to a deeper understanding of their chemical behavior (Rybalova et al., 2008).

Chemical Reactions and Properties

• Trifluoromethylated pyridines can be synthesized through various chemical reactions, including catalytic asymmetric 1,3-dipolar cycloadditions (Li et al., 2011).
• Reactions with diazo compounds and 1,3-dipolar cycloadditions involving derivatives of 3,3,3-trifluoropropene produce various trifluoromethyl-substituted compounds (Plancquaert et al., 1996).

Physical Properties Analysis

• The physical properties of 3-(Trifluoromethyl)pyridine derivatives, including their spectroscopic and structural characteristics, are essential for understanding their reactivity and potential applications (Evecen et al., 2017).

Chemical Properties Analysis

• The chemical properties, such as reactivity and stability, of 3-(Trifluoromethyl)pyridine derivatives are influenced by their molecular structure and substituents (Sugihara et al., 1996).
• Studies on the synthesis, characterization, and computational modeling of various pyridinium salts provide insights into their chemical properties and potential applications in organic synthesis (Shapiro et al., 2018).

Scientific Research Applications

• Agrochemical Industry

  • Summary of Application : 3-(Trifluoromethyl)pyridine (TFMP) and its derivatives are used in the protection of crops from pests. Fluazifop-butyl was the first TFMP derivative introduced to the agrochemical market.
  • Results or Outcomes : Since the introduction of Fluazifop-butyl, more than 20 new TFMP-containing agrochemicals have acquired ISO common names.

• Pharmaceutical Industry

  • Summary of Application : Several TFMP derivatives are used in the pharmaceutical and veterinary industries.
  • Results or Outcomes : Five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

• Synthesis of Metal-Organic Frameworks (MOFs)

  • Summary of Application : 3-(Trifluoromethyl)pyridine is used in the synthesis of metal-organic frameworks (MOFs).

• Pesticide Development

  • Summary of Application : TFMP and its intermediates have gained a fundamental role as key structural ingredients for the development of many agrochemical compounds. They are used in the development of pesticides that not only prevent crop losses caused by parasites, but also protect human populations from the spread of diseases such as malaria, dengue fever, or the Zika virus, all of which are carried by mosquitoes.

• Fungicide Development

  • Summary of Application : TFMP is used in the synthesis of fungicides. It was found that the trifluoromethyl-substituted pyridine derivative showed higher fungicidal activity than chlorine and other derivatives.

• Synthesis of Methiodide Salts

  • Summary of Application : 3-(Trifluoromethyl)pyridine is used in the synthesis of methiodide salts.

• Development of Fluorinated Organic Chemicals

  • Summary of Application : TFMP and its intermediates are important ingredients for the development of fluorinated organic chemicals. The effects of fluorine and fluorine-containing moieties on the biological activities and physical properties of compounds have earned fluorine a unique place in the arsenal of the discovery chemist.

• Synthesis of Fluazinam

  • Summary of Application : TFMP is used in the synthesis of fluazinam. It was found that the trifluoromethyl-substituted pyridine derivative showed higher fungicidal activity than chlorine and other derivatives.

• Reduction of Production Costs

  • Summary of Application : TFMP products can be reduced to 3-(trifluoromethyl)pyridine (3-TF) by catalytic hydrogenolysis and then fed back into the reactor to reduce overall production costs.

Safety And Hazards

When handling 3-(Trifluoromethyl)pyridine, it is recommended to wear suitable protective clothing and avoid contact with skin and eyes. Avoid formation of dust and aerosols. Use non-sparking tools.

Future Directions

The demand for TFMP derivatives has been increasing steadily in the last 30 years. It is expected that many novel applications of TFMP will be discovered in the future. Currently, the major use of TFMP derivatives is in the protection of crops from pests.

More Information