Pyridine-N-oxide

Pyridine-N-oxide
IUPAC name

Pyridine-N-oxide
Other names

pyridine-1-oxide
Identifiers
CAS number 694-59-7 Y
PubChem 12753
ChemSpider 12229 Y
ChEBI CHEBI:29136 Y
Jmol-3D images Image 1
Properties
Molecular formula C5H5NO
Molar mass 95.1 g mol−1
Appearance colourless solid
Melting point

65–66 °C
Boiling point

270 °C, 543 K, 518 °F
Solubility in water high
Basicity (pKb) 0.8
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1] The molecule is planar. The compound is used infrequently as an oxidizing reagent in organic synthesis.[2] It also serves as a ligand in coordination chemistry.

Synthesis

The oxidation of pyridine is effected with peracetic acid, a reaction that affords the protonated derivative. Subsequent treatment with base liberates the neutral oxide.[3]

Safety

The compound is a skin irritant.

References

  1. ^ J. Meisenheimer (1926). "Über Pyridin-, Chinolin- und Isochinolin-N-oxyd". Berichte der deutschen chemischen Gesellschaft 59 (8): 1848–1853. doi:10.1002/cber.19260590828. 
  2. ^ 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
  3. ^ H. S. Mosher, L. Turner, and A. Carlsmith (1963), "Pyridine-N-oxide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0828 ; Coll. Vol. 4: 828