112110-07-3 | 5-Trifluoromethyl-pyridin-3-ylamine

CAS:112110-07-3 | 5-Trifluoromethyl-pyridin-3-ylamine,Description

Synthesis Analysis

The synthesis of 5-(Trifluoromethyl)pyridin-3-amine and related compounds involves several key steps, including the displacement of a halogen atom with trimethylamine gas and anion replacement with a triflate counter-ion. These steps are critical for achieving high yields and ensuring the incorporation of the trifluoromethyl group into the pyridin-3-amine framework. This process has been demonstrated in the preparation of precursors for radiolabeling peptides for PET imaging, highlighting its significance in nuclear medicine (Davis & Fettinger, 2018).

Molecular Structure Analysis

X-ray crystallography has been employed to determine the molecular structure of related compounds, providing insights into their chemical behavior. For instance, the structure of trans-[Co(III)(bpb)(amine)2]X demonstrates how coordination chemistry can be utilized to synthesize complexes with specific molecular architectures (Amirnasr, Schenk, & Meghdadi, 2002). Such analyses are vital for understanding the reactivity and potential applications of these compounds.

Chemical Reactions and Properties

Chemoselective synthesis methods have been developed for derivatives of 5-(Trifluoromethyl)pyridin-3-amine, demonstrating its versatility as a building block. These methods allow for the introduction of various functional groups, significantly expanding the utility of this compound in organic synthesis and medicinal chemistry (Aquino et al., 2015).

Scientific Research Applications

• Agrochemical and Pharmaceutical Industries

  • 5-(Trifluoromethyl)pyridin-3-amine and its derivatives are used in the agrochemical and pharmaceutical industries.
  • The major use of these derivatives is in the protection of crops from pests.
  • More than 20 new trifluoromethylpyridine (TFMP)-containing agrochemicals have acquired ISO common names.
  • Several TFMP derivatives are also used in the pharmaceutical and veterinary industries.
  • Five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval.

• Synthesis of Imidazo[1,2-a]pyridine-Coumarin Hybrid Molecules

  • 2-Amino-3-chloro-5-trifluoromethylpyridine, a derivative of 5-(Trifluoromethyl)pyridin-3-amine, acts as a reactant in the synthesis of novel imidazo[1,2-a]pyridine-coumarin hybrid molecules.
  • These hybrid molecules are potential inhibitors of NS5B in the treatment of Hepatitis C.

• Synthesis of Fluorinated Organic Chemicals

  • Fluorine-containing compounds significantly affect pharmaceutical growth, making up more than 50 percent of the best-selling drug molecules approved by the US Food and Drug Administration (FDA).
  • The trifluoromethyl (TFM, -CF3)-group-containing FDA-approved drugs for the last 20 years are summarized.
  • The review covers the detailed chemistry of 19 FDA-approved drugs in the past 20 years, which contains the TFM group as one of the pharmacophores.

• Development of New Insecticides and Pesticides

  • The trifluoromethylpyridine functional group is present in many pesticides and insecticides.
  • Amide and amine derivatives of trifluoromethylpyridine have been prepared from commercially available and inexpensive starting materials.
  • These molecules are very useful for the development of new insecticides and pesticides to improve therapeutic activity.

• Synthesis of Several Crop-Protection Products

  • 2,3-dichloro-5-(trifluoromethyl)pyridine (2,3,5-DCTF), a derivative of 5-(Trifluoromethyl)pyridin-3-amine, is used in the production of several crop-protection products.
  • It can be obtained by direct chlorination and fluorination of 3-picoline and followed by aromatic nuclear chlorination of the pyridine ring.
  • Notably, of all the TFMP derivatives, it is in highest demand.

• Development of Novel Insecticides and Pesticides

  • The trifluoromethylpyridine functional group is present in many pesticides and insecticides.
  • Amide and amine derivatives of trifluoromethylpyridine have been prepared from commercially available and inexpensive starting materials.
  • These molecules are very useful for the development of new insecticides and pesticides to improve therapeutic activity.

Safety And Hazards

5-(Trifluoromethyl)pyridin-3-amine is harmful by inhalation, in contact with skin, and if swallowed. In the event of a fire involving this material, use dry powder or carbon dioxide extinguishers.

Future Directions

It is expected that many novel applications of TFMP will be discovered in the future. The development of fluorinated organic chemicals is becoming an increasingly important research topic. More than 50% of the pesticides launched in the last two decades have been fluorinated.

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