5-(Trifluoromethyl)-2-pyridone

CAS Number 33252-63-0

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

5-(Trifluoromethyl)-2-pyridone CAS 33252-63-0

A fluorinated heterocyclic building block

Used as molecular scaffolds for drug discovery and ligands for catalytic reactions

Specifications | MSDS | Literature and Reviews

5-(Trifluoromethyl)-2-pyridone (CAS number 33252-63-0) is a trifluoromethyl substituted 2-pyridone. The tautomer of 5-(trifluoromethyl)-2-pyridone is 5-(trifluoromethyl)-2-hydroxypyridine in which its hydrogen locates on the oxygen. Fourier-transfer infrared (FT-IR) spectroscopy shows that in solid state 2-pyridone C=O stretching frequency is present while the O-H stretching is absent, indicating the hydrogen is closer to the nitrogen than the oxygen. 5-(Trifluoromethyl)-2-pyridone is heavily exploited in catalytic reactions, especially in palladium catalysed directives and non-directive sp³/sp² carbon-hydrogen activations. During the catalytic cycle, 5-(trifluoromethyl)-2-pyridone elongates the C-H bond with hydrogen bonding forming a 6-membered palladacycle intermediate.

5-(Trifluoromethyl)-2-pyridone serves as a hydrogen bond acceptor (ketone) and donor (amine), as well as a bioisostere for amides, benzenes, and pyridines, which is ideal for drug discovery. The trifluoromethyl group increases the lipophilicity of 5-(trifluoromethyl)-2-pyridone improving the permeability to the cell membranes.

Multiple functional groups

For facile synthesis

Fluorinated pyridone building block

For drug discovery, ligands, and organic synthesis

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

General Information

CAS Number	33252-63-0
Chemical Formula	C₆H₄F₃NO
Full Name	2-Hydroxy-5-(trifluoromethyl)pyridine
Molecular Weight	163.10 g/mol
Synonyms	5-(Trifluoromethyl)-2-pyridinol
Classification / Family	Fluorinated building blocks, Heterocyclic building blocks, Ligands, Catalytic reactions, APIs

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 145 °C – 149 °C
Appearance	White powder

MSDS Documentation

5-(Trifluoromethyl)-2-pyridone MSDS Sheet

Literature and Reviews

Pyridones in drug discovery: recent advances, Y. Zhang et al., Bioorg. Med. Chem., 38, 127849(2021); DOI: 10.1016/j.bmcl.2021.127849.
Design, synthesis and structure-activity evaluation of novel 2-pyridone-based inhibitors of α-synuclein aggregation with potentially improved BBB permeability, A. Mahía et al., Bioorg. Chem., 117, 105472(2021); DOI: 10.1016/j.bioorg.2021.105472.
Harnessing the efficacy of 2-pyridone ligands for Pd-catalyzed (β/γ)-C(sp³)─H activations, N. Mandal et al., J. Org. Chem., 85(20), 13228–13238(2020); DOI: 10.1021/acs.joc.0c02210.

Ligand-accelerated non-directed C–H functionalization of arenes, P. Wang et al., Nature, 551(7681), 489–493(2017); DOI: 10.1038/nature24632.
Recent advances in chemistry and pharmacological aspects of 2-pyridone scaffolds, M. Amer et al., J. Saudi Chem. Soc., 25(6), 101259(2021); DOI: 10.1016/j.jscs.2021.101259.