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Cyclooctatetraene (CAS 629-20-9)

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Alternate Names:
1,3,5,7-Cyclooctatetraene
Application:
Cyclooctatetraene is an anti-aromatic hydrocarbon with polyolefin-like behavior
CAS Number:
629-20-9
Molecular Weight:
104.15
Molecular Formula:
C8H8
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Cyclooctatetraene is an anti-aromatic hydrocarbon with 8 delocalized p-electrons that adopts a non-planar boat conformation with polyolefin-like behavior. Cyclooctatetraene is used in liquid state organic dye lasers, and as a triplet state qunecher to reduce dye blinking. It has the ability to fluoresce.Cyclooctatetraene is used as a reactant in the synthesis of tricyclo[4.2.2.02,5]dec-9-ene-3,4,7,8-tetracarboxylic acid diimide.


Cyclooctatetraene (CAS 629-20-9) References

  1. Cyclooctatetraene dianion--an artifact?  |  Dominikowska, J. and Palusiak, M. 2011. J Comput Chem. 32: 1441-8. PMID: 21274857
  2. The Planar Cyclooctatetraene Bridge in Bis-Metallic Macrocycles: Isolating or Conjugating?  |  Bhowmik, S., et al. 2017. Inorg Chem. 56: 2287-2296. PMID: 28182414
  3. Stabilizing a different cyclooctatetraene stereoisomer.  |  Li, L., et al. 2017. Proc Natl Acad Sci U S A. 114: 9803-9808. PMID: 28847954
  4. A study of the aromaticity of heteroannelated cyclooctatetraene derivatives.  |  Abdukadir, A., et al. 2018. J Mol Model. 24: 123. PMID: 29721619
  5. Cyclooctatetraene: A Bioactive Cubane Paradigm Complement.  |  Xing, H., et al. 2019. Chemistry. 25: 2729-2734. PMID: 30681236
  6. Europium Cyclooctatetraene Nanowire Carpets: A Low-Dimensional, Organometallic, and Ferromagnetic Insulator.  |  Huttmann, F., et al. 2019. J Phys Chem Lett. 10: 911-917. PMID: 30717591
  7. Photochemical Cyclopropanation of Cyclooctatetraene and (Poly-)unsaturated Carbocycles.  |  Guo, Y., et al. 2020. Org Lett. 22: 5126-5130. PMID: 32551700
  8. Reduction of π-Expanded Cyclooctatetraene with Lithium: Stabilization of the Tetra-Anion through Internal Li+ Coordination.  |  Zhou, Z., et al. 2021. Angew Chem Int Ed Engl. 60: 3510-3514. PMID: 33108043
  9. Graphene-induced planarization of cyclooctatetraene derivatives.  |  Kroeger, AA. and Karton, A. 2022. J Comput Chem. 43: 96-105. PMID: 34677827
  10. Two Steps to Bicyclo[4.2.0]octadienes from Cyclooctatetraene: Total Synthesis of Kingianic Acid A.  |  Patel, HD. and Fallon, T. 2022. Org Lett. 24: 2276-2281. PMID: 35293754
  11. Cation Complexes of Uranium and Thorium with Cyclooctatetraene: Photochemistry and Decomposition Products.  |  Marks, JH., et al. 2022. J Phys Chem A. 126: 4230-4240. PMID: 35749286
  12. Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative.  |  Kumar, R., et al. 2022. Angew Chem Int Ed Engl. 61: e202207486. PMID: 35819871
  13. [8]Cyclo-para-phenylmethine as a Super-Cyclooctatetraene: Dynamic Behavior, Global Aromaticity, and Open-Shell Diradical Character in the Neutral and Dicationic States.  |  Li, Z., et al. 2022. Angew Chem Int Ed Engl. 61: e202210697. PMID: 36008354
  14. Transition-State Spectroscopy of Cyclooctatetraene.  |  Wenthold, PG., et al. 1996. Science. 272: 1456-9. PMID: 8662467

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Cyclooctatetraene, 1 g

sc-257273
1 g
$64.00