4-Picoline-N-oxide

Chemical Properties

ALMOST WHITE TO BROWN FINE CRYSTALLINE POWDER

Uses

4-Picoline-N-oxide serves as a precursor for the synthesis of pyridine-4-ylmethyl acetate using acetic anhydride[1]. It functions as an external oxidant in ruthenium-catalyzed oxidative amidation of alkynes to primary and secondary amides[2][3]. The compound is employed as a ligand material in aqueous solutions with terbium or dysprosium chlorides[4].

Purification Methods

Recrystallise the N-oxide from EtOH/EtOAc, Me2CO/Et2O or *C6H6. [Bullitt & Maynard J Am Chem Soc 76 1370 1954, Boekelheide & Linn J Am Chem Soc 76 1286 1954]. [Beilstein 20 III/IV 2741, 20/5 V 558.]

References

[1]Zhu, Y., Leng, Y., Xu, J., & Chen, N. (2025). Boekelheide Rearrangement: A Promising Tool for the Modification of Aromatic Azaheterocycles. ChemistrySelect, 10(35). https://doi.org/10.1002/slct.202504047
[2]Santos, A. S., Silva, A. M. S., & Marques, M. M. B. (2020). Sustainable Amidation Reactions – Recent Advances. European Journal of Organic Chemistry, 2020(17), 2501–2516. https://doi.org/10.1002/ejoc.202000106
[3]Li, D., Lv, S., Qu, J., & Zhou, Y. (2020). Oxidation of 4-Aryl-1,1,1-trifluorobut-2-en-2-yl Trifluoro­methanesulfonates by 4-Picoline-N-Oxide: A Novel Approach to β-Trifluoromethyl-α,β-enones. Synthesis, 52(08), 1203–1210. https://doi.org/10.1055/s-0039-1690054
[4]Kuppusamy, S. K., Moreno-Pineda, E., Nonat, A. M., Heinrich, B., Karmazin, L., Charbonnière, L. J., & Ruben, M. (2023). Binuclear Lanthanide Complexes Based on 4-Picoline- <i>N</i> -oxide: From Sensitized Luminescence to Single-Molecule Magnet Characteristics. Crystal Growth &amp; Design, 23(2), 1084–1094. https://doi.org/10.1021/acs.cgd.2c01234