5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile
[CAS# 573762-62-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile
• Synonyms: 5-Amino-2-cyano-3-(trifluoromethyl)pyridine; 5-Amino-3-(trifluoromethyl)2-cyanopyridine
• Molecular Formula: C₇H₄F₃N₃
• Molecular Weight: 187.12
• CAS Registry Number: 573762-62-6
• EC Number: 815-137-9
• SMILES: C1=C(C=NC(=C1C(F)(F)F)C#N)N

Properties

• Solubility: Slightly soluble (1.5 g/L) (25 °C), Calc.^*
• Density: 1.45±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301-H412
• Safety Statements: P264-P270-P273-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile is a notable chemical compound in the realm of organic chemistry, particularly valued for its versatility in synthesis and its applications in medicinal chemistry. This compound, with a trifluoromethyl group and a carbonitrile moiety attached to a pyridine ring, exhibits unique chemical properties that make it a useful building block for various chemical transformations.

The discovery of 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile can be traced to the study of pyridine derivatives and their reactions. Pyridine, a six-membered aromatic ring containing one nitrogen atom, has long been of interest due to its ability to participate in a range of chemical reactions. The introduction of substituents such as amino, trifluoromethyl, and carbonitrile groups to the pyridine ring further enhances its reactivity and utility.

The synthesis of 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile generally involves multiple steps. One common method is the introduction of the trifluoromethyl group to the pyridine ring, followed by nitration to achieve the carbonitrile group. The amino group can be introduced through various amination processes. The precise control over these substituents allows chemists to tailor the properties of the compound for specific applications.

In medicinal chemistry, 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile has been explored for its potential as a pharmaceutical intermediate. The trifluoromethyl group is known for enhancing the metabolic stability and biological activity of compounds. The presence of the amino and carbonitrile groups also contributes to its potential as a bioactive molecule. Research has focused on utilizing this compound in the development of drugs with improved efficacy and selectivity.

The compound’s utility extends to the field of agrochemicals as well. In the development of herbicides and pesticides, 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile can be used to create molecules with enhanced activity against specific pests or weeds. The trifluoromethyl group, in particular, is known for its ability to modify the biological activity of agrochemical agents.

Additionally, the compound has applications in materials science. The trifluoromethyl and carbonitrile groups provide useful functionalities for the development of advanced materials, including those used in electronic and optical devices. The chemical reactivity of 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile allows for the synthesis of novel materials with specific properties, such as improved conductivity or stability.

In summary, 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile is a versatile chemical substance with significant applications across medicinal chemistry, agrochemicals, and materials science. Its unique combination of trifluoromethyl, amino, and carbonitrile groups makes it a valuable building block in the synthesis of complex molecules and materials, highlighting its importance in both research and industry.

References

2023. Forced Degradation of an Anticancer Drug Apalutamide: Impurity Profiling and Structure Elucidation Study. Chromatographia, 86(11-12).
DOI: 10.1007/s10337-023-04294-9

2018. Apalutamide. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0218