2-Amino-4-(trifluoromethyl)pyridine
[CAS# 106447-97-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Methylpyridine
• Name: 2-Amino-4-(trifluoromethyl)pyridine
• Synonyms: 4-Trifluoromethyl-2-pyridinamine
• Molecular Formula: C₆H₅F₃N₂
• Molecular Weight: 162.11
• CAS Registry Number: 106447-97-6
• EC Number: 634-596-4
• SMILES: C1=CN=C(C=C1C(F)(F)F)N

Properties

• Melting point: 72-73 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H300-H314-H5-H7-H8-H9-H335
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	2	H300
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331

Discovery and Applications

2-Amino-4-(trifluoromethyl)pyridine, often abbreviated as 2-amino-4-TFMP, is an aromatic heterocyclic compound of great importance in both synthetic chemistry and pharmacology. Its unique chemical structure gives it valuable properties that can be used in a variety of applications.

2-Amino-4-(trifluoromethyl)pyridine compounds are synthesized as part of the study of pyridine derivatives and their potential applications. Pyridine is a basic aromatic heterocyclic ring that serves as a core structure, while the introduction of amino and trifluoromethyl substituents at specific positions enhances the chemical reactivity and stability of the molecule. In particular, the trifluoromethyl group is known for its electron-withdrawing properties, which significantly affect the chemical behavior of the compound.

2-Amino-4-(trifluoromethyl)pyridine has several important properties: The trifluoromethyl group significantly affects the electronic properties of the pyridine ring, making the compound more reactive in certain chemical reactions. This reactivity can be used to synthesize a variety of organic compounds and drugs. In drug development, 2-amino-4-TFMP is valued for its role as an intermediate in the synthesis of biologically active molecules. Its unique structure enables it to participate in reactions that lead to the formation of compounds with therapeutic potential. It is used to develop drugs for a variety of diseases, including those involving the nervous and cardiovascular systems. The reactivity of this compound can also be used in materials science. It is used to create functionalized materials and polymers with desired properties, such as increased stability and resistance to degradation. The trifluoromethyl group, in particular, enhances the chemical and thermal stability of materials.

2-Amino-4-(trifluoromethyl)pyridine is a key building block in the synthesis of pharmaceutical compounds. Its chemical structure can be used to develop new drugs with specific biological activities. Research continues to explore its potential in creating new therapeutic agents.

The compound is used as an intermediate in various chemical syntheses. Its reactivity helps generate complex organic molecules, which are essential for research and industrial applications.

In materials science, 2-amino-4-TFMP helps in the development of advanced materials. Its incorporation into polymers and resins enhances the properties of these materials, making them suitable for specialized applications in electronics and coatings.

References

2023. Open science discovery of potent noncovalent SARS-CoV-2 main protease inhibitors. Science (New York, N.Y.), 382(6671), eabo7201.
DOI: 10.1126/science.abo7201

2000. Substituted 2-aminopyridines as inhibitors of nitric oxide synthases. Bioorganic & Medicinal Chemistry Letters, 10(17), 1947-1950.
DOI: 10.1016/s0960-894x(00)00389-9

2022. Reactions of Tetramethyl Ethynyldiphosphonate with Substituted 2-Aminopyridines. Russian Journal of General Chemistry, 92(11), 2327-2332.
DOI: 10.1134/s107036322211010x