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9-Oxabicyclo[6.1.0]non-4-ene (CAS 637-90-1)

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Alternate Names:
1,2-Epoxy-5-cyclooctene
CAS Number:
637-90-1
Purity:
≥98%
Molecular Weight:
124.18
Molecular Formula:
C8H12O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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9-Oxabicyclo[6.1.0]non-4-ene, also referred to as 9-oxabicyclononane, is a bicyclic hydrocarbon featuring a sole oxygen atom at the 9th carbon position. This molecule finds extensive application in various scientific research endeavors, owing to its remarkable versatility. Notably, 9-Oxabicyclo[6.1.0]non-4-ene serves as a highly reactive building block for the synthesis of diverse compounds, making it invaluable in the realms of chemistry, biochemistry, and pharmacology. Its distinctive structure and properties render it particularly suitable for investigations within these fields. In scientific research, 9-Oxabicyclo[6.1.0]non-4-ene assumes multiple roles. Foremost, it acts as a component for organic synthesis, enabling the creation of pharmaceuticals, agrochemicals, and materials. Additionally, it serves as a catalyst in organic reactions, including the Diels-Alder reaction and the Wittig reaction. Moreover, 9-Oxabicyclo[6.1.0]non-4-ene can function as a starting material for the synthesis of polycyclic aromatic hydrocarbons, which hold significance in materials science and nanotechnology. Its high reactivity allows it to catalyze a diverse range of chemical reactions. The mechanism of action of 9-Oxabicyclo[6.1.0]non-4-ene depends on the specific reaction at hand. In the Diels-Alder reaction, it acts as a Lewis acid, facilitating the formation of a new bond between reactants. Conversely, in the Wittig reaction, it acts as a nucleophile, aiding in the formation of a new bond between reactants.


9-Oxabicyclo[6.1.0]non-4-ene (CAS 637-90-1) References

  1. Synthesis, molecular modeling, and opioid receptor affinity of 9, 10-diazatricyclo[4.2.1.1(2,5)]decanes and 2,7-diazatricyclo[4.4.0. 0(3,8)]decanes structurally related to 3,8-diazabicyclo[3.2. 1]octanes.  |  Vianello, P., et al. 2000. J Med Chem. 43: 2115-23. PMID: 10841790
  2. Intramolecular bromonium ion assisted epoxide ring-opening: capture of the oxonium ion with an added external nucleophile.  |  Bonney, KJ., et al. 2011. J Org Chem. 76: 97-104. PMID: 21114250
  3. High-yielding, two-step 18F labeling strategy for 18F-PARP1 inhibitors.  |  Keliher, EJ., et al. 2011. ChemMedChem. 6: 424-7. PMID: 21360818
  4. Force-rate characterization of two spiropyran-based molecular force probes.  |  Gossweiler, GR., et al. 2015. J Am Chem Soc. 137: 6148-51. PMID: 25916203
  5. Enhanced polymer mechanical degradation through mechanochemically unveiled lactonization.  |  Lin, Y., et al. 2020. Nat Commun. 11: 4987. PMID: 33020488
  6. Substituent Effects in Mechanochemical Allowed and Forbidden Cyclobutene Ring-Opening Reactions.  |  Brown, CL., et al. 2021. J Am Chem Soc. 143: 3846-3855. PMID: 33667078
  7. Stereoselective synthesis of cyclic ethers via bromine assistedepoxide ring expansion  |  Davies, S. G., Polywka, M. E., & Thomas, S. E. 1985. Tetrahedron letters. 26(11): 1461-1464.
  8. Synthesis of cyclic ethers via bromine assisted epoxide ring expansion  |  Davies, S. G., Polywka, M. E., & Thomas, S. E. 1986. Journal of the Chemical Society, Perkin Transactions 1. 0: 1277-1282.
  9. Transannular oxygen participation in halofluorination reactions of 9-oxabicyclo[6.1.0]non-4-ene[1]  |  Haufe, G., Alvernhe, G., & Laurent, A. 1990. Journal of fluorine chemistry. 46(1): 83-95.
  10. Tricyclic oxonium-directed addition: Regiochemistry and stereochemistry of the iodination reactions in 2,3-epoxy cyclooct-5-en-1-ols and 2,3-epoxy-5-en-1-one.  |  Alvarez, E., Diaz, M. T., Rodríguez, M. L., & Martín, J. D. 1990. Tetrahedron letters. 31(11): 1629-1632.
  11. Tailored Ring-Opening Metathesis Polymerization Derived Monolithic Media Prepared from Cyclooctene-Based Monomers and Cross-Linkers  |  Bandari, R., Prager-Duschke, A., Kühnel, C., Decker, U., Schlemmer, B., & Buchmeiser, M. R. 2006. Macromolecules. 39(16): 5222-5229.
  12. Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution  |  Revunov, E., & Zhuravlev, F. 2013. Journal of Fluorine Chemistry. 156: 130-135.
  13. Oxidation reaction and thermal stability of 1,3-butadiene under oxygen and initiator  |  Liang, M., Zhao, H., Dai, S., Yu, C., Cheng, H., Li, W.,.. & Liu, X. 2022. Arabian Journal of Chemistry. 15(11): 104289.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

9-Oxabicyclo[6.1.0]non-4-ene, 5 g

sc-257025
5 g
$200.00