3-(Trifluoromethyl)-2-pyridone

CAS Number 22245-83-6

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

3-(Trifluoromethyl)-2-pyridone CAS 22245-83-6

A fluorinated heterocyclic building block

Used as a synthesis intermediate for ligands and bioactive ingredients in application of drug discovery and catalytic reactions

Overview
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3-(Trifluoromethyl)-2-pyridone (CAS number 22245-83-6), also known as 2-hydroxy-3-(trifluoromethyl)pyridine, is a trifluoromethyl substituted 2-hydroxypyridine. In catalytic reactions, the amide group of 2-pyridone binds to transition metals forming stable 5-/6-membred ring intermediates. Therefore, 3-(trifluoromethyl)-2-pyridone is extensively used as ligands in catalytic reaction such as directed C-H activation on meta-position. The trifluoromethyl substituent of 3-(trifluoromethyl)-2-pyridone tunes its metal-binding affinity and limits the reaction site for improving regioselectivity.

Many derivatives of 2-pyridone are bioactive such as Doravirine a non-nucleoside reverse transcriptase inhibitor for treatment of AIDS. An imidazoline derivative containing 2-pyridone is evaluated as neuropeptide-Y receptor Y5 antagonists and it displays significant inhibition of food intake for treatment of diet-induced obesity.

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	22245-83-6
Chemical Formula	C₆H₄F₃NO
Full Name	2-Hydroxy-3-(trifluoromethyl)pyridine
Molecular Weight	163.10 g/mol
Synonyms	3-(Trifluoromethyl)pyridin-2-ol
Classification / Family	Fluorinated building blocks, Heterocyclic building blocks, Ligands, Catalytic reactions, APIs

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 150 °C – 155 °C
Appearance	Off-white to pale purple powder

MSDS Documentation

3-(Trifluoromethyl)-2-pyridone MSDS Sheet

Literature and Reviews

De novo generation of a bright blue fluorophore from 2-oxoglutarate in biological samples, Y. Kim et al., Chem. Sci., 13, 365(2022); DOI: DOI: 10.1039/d1sc05808h.
Discovery of pyridone-containing imidazolines as potent and selective inhibitors of neuropeptide Y Y5 receptor, M. Ando et al., Bioorg. Med. Chem., 17, 6106–6122(2009); DOI: 10.1016/j.bmc.2009.05.069.
Ligand-promoted meta-C-H functionalization of benzylamines, P. Wang et al., Angew. Chem. Int. Ed. Engl., 56(18), 5125–5129(2017); DOI: 10.1002/anie.201701803.
Optimum bifunctionality in a 2-(2-pyridyl-2-ol)-1,10-phenanthroline based ruthenium complex for transfer hydrogenation of ketones and nitriles: impact of the number of 2-hydroxypyridine fragments, B. Paul et al., Dalton Trans., 45, 11162(2016); DOI: 10.1039/c6dt01961g.
Low cost carbazole-based organic dyes bearing the acrylamide and 2-pyridone moieties for efficient dye-sensitized solar cells, M. Eltoukhi et al., J. Photochem. Photobiol. A, 426, 113760(2022); DOI: 10.1016/j.jphotochem.2021.113760.

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