Pyridine-N-oxide

Pyridine-N-oxide

chembox new
ImageFile=PyO'.pngImageSize= 100
IUPACName= Pyridine-N-oxide
OtherNames= pyridine-1-oxide
Section1=Chembox Identifiers
CASNo= 694-59-7
PubChem= 24888050
SMILES=
Section2=Chembox Properties
C=5 | H = 5 | N = 1 | O = 1
MolarMass= 95.10
Appearance= colourless solid
Density=
MeltingPt= 65–66 °C
BoilingPt= 270 °C
Solubility= high

Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peracids as the oxidising agent. [cite journal | author = J. Meisenheimer | title = Über Pyridin-, Chinolin- und Isochinolin-N-oxyd | journal = Berichte der deutschen chemischen Gesellschaft | volume = 59 | pages = 1848 – 1853 | doi = 10.1002/cber.19260590828 | year = 1926] The molecule is planar. The compound is used infrequently as an oxidizing reagent in organic synthesis. [S. Nicholas Kilényi "Pyridine N-Oxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons, New York. DOI|10.1002/047084289X.rp283 Article Online Posting Date: April 15, 2001] It also serves as a ligand in coordination chemistry.

ynthesis

The oxidation of pyridine is effected with peracetic acid, a reaction that affords the protonated derivative. Subsequent treatment with base liberates the neutral oxide. [OrgSynth | author = H. S. Mosher, L. Turner, and A. Carlsmith | title = Pyridine-N-oxide | collvol = 4 | collvolpages = 828 | year = 1963 | prep = cv4p0828]

afety

The compound is a skin irritant.

References


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