79456-34-1 | 2-Amino-5-bromo-3-(trifluoromethyl)pyridine

CAS:79456-34-1 | 2-Amino-5-bromo-3-(trifluoromethyl)pyridine,Description

5-Bromo-3-(trifluoromethyl)pyridin-2-amine is a compound of interest in various chemical research areas due to its potential applications in medicinal chemistry and material science. The presence of bromine and trifluoromethyl groups attached to the pyridine ring makes it a versatile intermediate for further chemical modifications and synthesis of more complex molecules.

Synthesis Analysis

The synthesis of related brominated pyridine compounds has been explored in several studies. For instance, the regioselective displacement reaction of ammonia with 5-bromo-2,4-dichloro-6-methylpyrimidine resulted in the formation of 5-bromo-2-chloro-6-methylpyrimidin-4-amine, which could be further reacted with secondary amines to afford substituted aminopyrimidines. Another study demonstrated the synthesis of 2-amino-5-[18F]fluoropyridines through a palladium-catalyzed reaction, starting from a bromopyridine precursor. These methodologies highlight the reactivity of bromopyridines and their utility in synthesizing nitrogen-containing heterocycles.

Molecular Structure Analysis

The molecular structure of bromopyridine derivatives has been characterized using various spectroscopic techniques. X-ray crystallography analysis has been employed to determine the crystalline structure of these compounds, revealing details such as space groups and hydrogen bonding patterns within the crystal lattice. Additionally, density functional theory (DFT) studies have been used to predict the optimized geometric structure and vibrational frequencies of 5-Bromo-2-(trifluoromethyl)pyridine, providing insights into its electronic properties.

Chemical Reactions Analysis

Bromopyridines are known to participate in various chemical reactions, including carbon-carbon coupling and substitution reactions. The presence of a bromine atom makes them suitable for cross-coupling reactions, which are essential in the synthesis of complex organic molecules. The reactivity of these compounds with amines has also been explored, leading to the formation of various aminopyridine derivatives.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-Bromo-2-(trifluoromethyl)pyridine have been studied using spectroscopic methods such as FT-IR and NMR. These techniques provide information on the chemical environment of the atoms within the molecule. Computational methods, including DFT and time-dependent DFT (TD-DFT), have been used to calculate properties like vibrational frequencies, chemical shifts, and non-linear optical (NLO) properties. The HOMO-LUMO energies and second-order interaction energies derived from NBO analysis contribute to understanding the molecule's reactivity and stability.

Case Studies and Applications

The antimicrobial activities of 5-Bromo-2-(trifluoromethyl)pyridine have been tested, indicating potential applications in developing new antimicrobial agents. Additionally, the interaction of this compound with pBR322 plasmid DNA has been monitored, suggesting its relevance in studies related to DNA interactions. These case studies demonstrate the practical applications of bromopyridine derivatives in biological systems.

Scientific Research Applications

• Agrochemical Industry

  • Summary of Application : TFMP derivatives are widely used in the agrochemical industry for the protection of crops from pests. Fluazifop-butyl was the first TFMP derivative introduced to the agrochemical market.
  • Methods of Application : While the specific methods of application for each agrochemical may vary, they are generally applied to crops in a manner that targets the pests affecting those crops.
  • Results or Outcomes : More than 20 new TFMP-containing agrochemicals have acquired ISO common names. The presence of fluorine and pyridine structure in TFMP derivatives result in superior pest control properties when compared to traditional phenyl-containing insecticides.

• Pharmaceutical Industry

  • Summary of Application : Several TFMP derivatives are used in the pharmaceutical industry. Five pharmaceutical products containing the TFMP moiety have been granted market approval.
  • Methods of Application : The specific methods of application or experimental procedures would depend on the specific pharmaceutical product and its intended use.
  • Results or Outcomes : Many candidates containing the TFMP moiety are currently undergoing clinical trials.

• Veterinary Industry

  • Summary of Application : TFMP derivatives are also used in the veterinary industry. Two veterinary products containing the TFMP moiety have been granted market approval.
  • Methods of Application : The specific methods of application or experimental procedures would depend on the specific veterinary product and its intended use.
  • Results or Outcomes : Many candidates containing the TFMP moiety are currently undergoing clinical trials.

• Functional Materials Fields

  • Summary of Application : Many recent advances in the functional materials fields have been made possible by the development of organic compounds containing fluorine.
  • Methods of Application : The specific methods of application or experimental procedures would depend on the specific functional material and its intended use.
  • Results or Outcomes : As the number of applications for these compounds continues to grow, the development of fluorinated organic chemicals is becoming an increasingly important research topic.

• Key Intermediate in Drug Synthesis

  • Summary of Application : The compound “5-Bromo-3-(trifluoromethyl)pyridin-2-amine” is a key intermediate in the atroposelective synthesis of the potent KRAS G12C covalent inhibitor divarasib (GDC-6036).
  • Methods of Application : The specific methods of application or experimental procedures would depend on the specific drug synthesis process.
  • Results or Outcomes : The successful synthesis of divarasib (GDC-6036) demonstrates the potential of this compound as a key intermediate in drug synthesis.

• Development of Fluorinated Organic Chemicals

  • Summary of Application : Many recent advances in the agrochemical, pharmaceutical, and functional materials fields have been made possible by the development of organic compounds containing fluorine.
  • Methods of Application : The specific methods of application or experimental procedures would depend on the specific development process of fluorinated organic chemicals.
  • Results or Outcomes : As the number of applications for these compounds continues to grow, the development of fluorinated organic chemicals is becoming an increasingly important research topic.

Safety And Hazards

The compound has been classified as Acute Tox. 3 Oral. The hazard statements include H301. The precautionary statements include P301 + P310. It should be stored in a dark place, in an inert atmosphere, at room temperature.

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