Isoxazole
Appearance
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Names | |
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IUPAC name
isoxazole
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.472 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C3H3NO | |
Molar mass | 69.06202 |
Density | 1.075 g/ml |
Boiling point | 95 °C |
Acidity (pKa) | -3.0 (of conjugate acid) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isoxazole is an azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring.
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.
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
- ^ Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).