3-Chloro-5-(trifluoromethyl)pyridin-2-amine
[CAS# 79456-26-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Methylpyridine
• Name: 3-Chloro-5-(trifluoromethyl)pyridin-2-amine
• Synonyms: 3-Chloro-5-(trifluoromethyl)-2-pyridylamine; 2-Amino-3-chloro-5-trifluoromethylpyridine; 2,3,5-ACTF
• Molecular Formula: C₆H₄ClF₃N₂
• Molecular Weight: 196.56
• CAS Registry Number: 79456-26-1
• EC Number: 401-670-0
• SMILES: C1=C(C=NC(=C1Cl)N)C(F)(F)F

Properties

• Melting point: 84-94 °C
• Boiling point: 205 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H412
• Safety Statements: P261-P264-P270-P271-P273-P301+P317-P304+P340-P319-P330-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-Chloro-5-(trifluoromethyl)pyridin-2-amine is a chemical compound with significant relevance in organic synthesis, pharmaceuticals, and agrochemicals. The discovery and subsequent applications of this compound have underscored its versatility and importance in various scientific and industrial fields.

3-Chloro-5-(trifluoromethyl)pyridin-2-amine belongs to the class of halogenated pyridines. This compound features a chlorine atom and a trifluoromethyl group attached to a pyridine ring, with an amino group at the second position. The presence of these functional groups imparts unique chemical properties, making it a valuable building block for creating more complex molecules.

The synthesis of 3-Chloro-5-(trifluoromethyl)pyridin-2-amine typically involves halogenation and amination reactions. The trifluoromethyl group is particularly noteworthy for its electron-withdrawing properties, which significantly influence the reactivity and stability of the compound. These properties have been leveraged in various chemical syntheses, facilitating the development of new compounds with desirable characteristics.

In the pharmaceutical industry, 3-Chloro-5-(trifluoromethyl)pyridin-2-amine serves as an intermediate in the synthesis of several bioactive molecules. Its structure allows for the introduction of functional groups that can enhance the pharmacological activity of therapeutic agents. Researchers have explored its use in developing drugs for treating various diseases, including cancer, inflammation, and infectious diseases. The compound's ability to modulate biological pathways through its interaction with enzymes and receptors makes it a valuable tool in drug discovery.

The agrochemical industry also benefits from the unique properties of 3-Chloro-5-(trifluoromethyl)pyridin-2-amine. It is used to synthesize herbicides, fungicides, and insecticides that are more effective and selective. The trifluoromethyl group improves the bioavailability and persistence of these agrochemicals in the environment, enhancing their efficacy in protecting crops from pests and diseases.

Furthermore, 3-Chloro-5-(trifluoromethyl)pyridin-2-amine finds applications in material science. It can be used to create specialty materials with unique properties, such as enhanced thermal stability and resistance to degradation. These materials are employed in various high-tech applications, including electronics and advanced coatings.

References

2023. Open science discovery of potent noncovalent SARS-CoV-2 main protease inhibitors. Science (New York, N.Y.), 382(6671).
DOI: 10.1126/science.abo7201

2013. Synthesis and biological evaluation of glucagon-like peptide-1 receptor agonists. Archives of Pharmacal Research, 36(11).
DOI: 10.1007/s12272-013-0253-9

2008. 3-Chloro-5-(trifluoro-meth-yl)pyridin-2-amine. Acta crystallographica. Section E, Structure reports online, 64(1).
DOI: 10.1107/s1600536807060205