79456-26-1 | 3-Chloro-5-(trifluoromethyl)pyridin-2-amine

CAS:79456-26-1 | 3-Chloro-5-(trifluoromethyl)pyridin-2-amine,Description

2-Amino-3-chloro-5-(trifluoromethyl)pyridine is a significant compound in the field of chemistry, especially for its applications in synthesizing various organic compounds, including pharmaceuticals and agrochemicals. Its unique combination of functional groups makes it a versatile precursor in organic synthesis, enabling the formation of complex molecules through a variety of chemical reactions.

Synthesis Analysis

The synthesis of 2-Amino-3-chloro-5-(trifluoromethyl)pyridine involves several steps, including the use of nicotinamide as a starting material through processes such as Hofmann degradation, oxidative chlorination, and diazotization-alcoholysis. These methods have been optimized to enhance the yield and efficiency of the synthesis process (Zuo Hang-dong, 2010).

Molecular Structure Analysis

The molecular structure of 2-Amino-3-chloro-5-(trifluoromethyl)pyridine has been extensively studied using X-ray diffraction and density functional theory (DFT) calculations. These studies have provided insights into the optimized molecular structure, electronic configuration, and the spatial arrangement of atoms within the molecule, highlighting the influence of the trifluoromethyl and amino groups on its chemical reactivity and stability (R. Mohamed Asath et al., 2017).

Chemical Reactions and Properties

2-Amino-3-chloro-5-(trifluoromethyl)pyridine participates in various chemical reactions, including nucleophilic substitutions and cycloadditions, due to the presence of reactive functional groups. Its reactivity is further demonstrated in the synthesis of poly-substituted pyridines through tandem C-F bond cleavage protocols, showcasing its utility in creating complex organic molecules (Zixian Chen et al., 2010).

Scientific Research Applications

“2-Amino-3-chloro-5-(trifluoromethyl)pyridine” is a type of trifluoromethylpyridine (TFMP), which has been widely used in various fields, including agrochemical and pharmaceutical industries. Here are some applications of TFMP and its derivatives:

• Agrochemical Industry

  • TFMP derivatives are majorly used for the protection of crops from pests.
  • Fluazifop-butyl was the first TFMP derivative introduced to the agrochemical market.
  • More than 20 new TFMP-containing agrochemicals have acquired ISO common names.

• Pharmaceutical Industry

  • Several TFMP derivatives are used in the pharmaceutical industry.
  • Five pharmaceutical products containing the TFMP moiety have been granted market approval.
  • Many candidates are currently undergoing clinical trials.

• Veterinary Industry

  • Two veterinary products containing the TFMP moiety have been granted market approval.

• Synthesis of Metal-Organic Frameworks (MOFs)

  • TFMP is used in the synthesis of MOFs.

• Synthesis of Methiodide Salts

  • TFMP is used in the synthesis of methiodide salts.

• Regioexhaustive Functionalization

  • 2-Chloro-5-(trifluoromethyl)pyridine, a type of TFMP, is used as a model substrate to investigate the regioexhaustive functionalization.

• Synthesis of Trifluoromethylpyridyllithiums

  • Trifluoromethylpyridyllithiums are prepared via a metalation reaction.

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

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

• Synthesis of Several Crop-Protection Products

  • Among TFMP derivatives, 2,3-dichloro-5-(trifluoromethyl)-pyridine (2,3,5-DCTF), which is used as a chemical intermediate for the synthesis of several crop-protection products, is in the highest demand.

• Preparation of (Trifluoromethyl)pyridyllithiums

  • (Trifluoromethyl)pyridyllithiums are prepared via a metalation reaction.

• Synthesis of Metal-Organic Frameworks (MOFs)

  • This compound is used in the synthesis of MOFs.

• Synthesis of Methiodide Salts

  • It is used in the synthesis of methiodide salts.

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

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

• Synthesis of Several Crop-Protection Products

  • Among TFMP derivatives, 2,3-dichloro-5-(trifluoromethyl)-pyridine (2,3,5-DCTF), which is used as a chemical intermediate for the synthesis of several crop-protection products, is in the highest demand.

Safety And Hazards

This chemical is considered hazardous and is harmful if swallowed. It is also harmful to aquatic life with long-lasting effects. In case of ingestion, it is advised to call a poison center or doctor/physician.

Future Directions

The trifluoromethyl-substituted pyridine derivative showed higher fungicidal activity than chlorine and other derivatives. More agrochemicals and pharmaceuticals containing 2-Amino-3-chloro-5-(trifluoromethyl)pyridine are expected to be introduced to the market in the near future.

More Information