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Product Code B1641-25g
Price $125 ex. VAT

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A fluorinated heterocyclic building block

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

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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated pyridone building block

For drug discovery, ligands, and organic synthesis

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High purity 33252-63-0

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

5-(Trifluoromethyl)-2-pyridone chemical structure, CAS 33252-63-0
5-(Trifluoromethyl)-2-pyridone chemical structure, CAS 33252-63-0

Product Details

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

MSDS Documentation

5-(Trifluoromethyl)-2-pyridone5-(Trifluoromethyl)-2-pyridone MSDS Sheet

Literature and Reviews

  1. Pyridones in drug discovery: recent advances, Y. Zhang et al., Bioorg. Med. Chem., 38, 127849(2021); DOI: 10.1016/j.bmcl.2021.127849.
  2. 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.
  3. 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.
  4. Ligand-accelerated non-directed C–H functionalization of arenes, P. Wang et al., Nature, 551(7681), 489–493(2017); DOI: 10.1038/nature24632.
  5. 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.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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