ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine 4-Picoline-N-oxide

4-Picoline-N-oxide

Product Name4-Picoline-N-oxide
CAS1003-67-4
MFC6H7NO
MW109.13
EINECS213-712-3
MOL File1003-67-4.mol

Chemical Properties

Melting point	182-185 °C(lit.)
Boiling point	152°C 11mm
Density	1.1143 (rough estimate)
refractive index	1.5180 (estimate)
Flash point	149 °C
storage temp.	Store at +2°C to +8°C.
solubility	1000g/l
form	powder to crystal
pka	1.38±0.10(Predicted)
color	White to Light yellow to Light orange
PH	>7 (H2O, 25℃)Aqueous solution
Water Solubility	soluble
Sensitive	Hygroscopic
BRN	106329
InChI	1S/C6H7NO/c1-6-2-4-7(8)5-3-6/h2-5H,1H3
InChIKey	IWYYIZOHWPCALJ-UHFFFAOYSA-N
SMILES	Cc1cc[n+]([O-])cc1
CAS DataBase Reference	1003-67-4(CAS DataBase Reference)
NIST Chemistry Reference	Pyridine, 4-methyl-, 1-oxide(1003-67-4)
EPA Substance Registry System	Pyridine, 4-methyl-, 1-oxide (1003-67-4)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-24/25
WGK Germany	1
RTECS	UT5800000
F	3
TSCA	TSCA listed
HS Code	29333999
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
4-Methylpyridine 1-oxide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

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 & Design, 23(2), 1084–1094. https://doi.org/10.1021/acs.cgd.2c01234

4-Picoline-N-oxide

Chemical Properties

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MSDS

Usage And Synthesis

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