Isoxazole

Isoxazole

Names
IUPAC name isoxazole
Identifiers
CAS Registry Number	288-14-2 Y
ChEBI	CHEBI:35595 Y
ChEMBL	ChEMBL13257 Y
ChemSpider	8897 Y
InChI InChI=1S/C3H3NO/c1-2-4-5-3-1/h1-3H Y Key: CTAPFRYPJLPFDF-UHFFFAOYSA-N Y InChI=1/C3H3NO/c1-2-4-5-3-1/h1-3H Key: CTAPFRYPJLPFDF-UHFFFAOYAS
Jmol-3D images	Image
PubChem	9254
SMILES n1occc1
Properties
Chemical formula	C3H3NO
Molar mass	69.06202 g/mol
Density	1.075 g/ml
Boiling point	95 °C (203 °F; 368 K)
Acidity (pKa)	-3.0 (of conjugate acid) [1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Isoxazole is an azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the univalent radical derived from isoxazole.

Isoxazole rings are found in some natural products, such as ibotenic acid. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra). A derivative, furoxan, is a nitric oxide donor.

An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin.

The synthetic androgenic steroid danazol also has an isoxazole ring.

See also

• Oxazole, an analog with the nitrogen atom in position 3.
• Pyrrole, an analog without the oxygen atom.
• Furan, an analog without the nitrogen atom.
• Simple aromatic rings

References

External links

• Synthesis of isoxazoles (overview of recent methods)