4-(Trifluoromethyl)nicotinic acid CAS 158063-66-2

Description:

4-(Trifluoromethyl)nicotinic acid, identified by CAS number 158063-66-2, is a specialized organic compound. It is a derivative of nicotinic acid (also known as niacin or vitamin B3), distinguished by the presence of a trifluoromethyl group (-CF<sub>3</sub>) at the 4-position of the pyridine ring. This substitution significantly influences the electronic properties and lipophilicity of the molecule, making it a valuable building block in medicinal chemistry and materials science. Typically appearing as a white to off-white solid, this compound is often utilized as an intermediate in the synthesis of more complex, biologically active molecules and functional materials. Its unique structure allows for diverse chemical modifications and incorporation into various molecular frameworks.

Properties:

Property Value
CAS Number 158063-66-2
Chemical Formula C7H4F3NO2
Molar Mass 191.11 g/mol
Appearance White to off-white crystalline powder or solid
Melting Point Approximately 200-205 °C (may vary)
Solubility Soluble in some organic solvents like methanol, DMSO; limited solubility in water
Synonyms 4-Trifluoromethylpyridine-3-carboxylic acid, 4-(Trifluoromethyl)-3-pyridinecarboxylic acid
IUPAC Name 4-(trifluoromethyl)pyridine-3-carboxylic acid

Usage:

4-(Trifluoromethyl)nicotinic acid serves primarily as a crucial intermediate and building block in organic synthesis, particularly in the development of novel pharmaceutical compounds and agrochemicals. The trifluoromethyl group often enhances metabolic stability, bioavailability, or binding affinity of the target molecules.

Examples of its applications include:

  • Pharmaceutical Research: Used in the synthesis of potential drug candidates. The trifluoromethyl-substituted pyridine core is a common motif in compounds designed to interact with biological targets such as enzymes and receptors.
  • Medicinal Chemistry: Employed to create derivatives for screening in various therapeutic areas, including oncology, inflammation, and neurodegenerative disorders.
  • Agrochemical Synthesis: Utilized in the development of new pesticides (insecticides, herbicides, fungicides) where the -CF<sub>3</sub> group can contribute to increased efficacy or altered spectrum of activity.
  • Material Science: Investigated for its potential incorporation into advanced materials, leveraging the unique properties imparted by the fluorinated group.
  • Chemical Reagent: Acts as a precursor for more complex fluorinated heterocyclic compounds used in various research and industrial applications.

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