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Benzocyclobutadiene

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Not to be confused with benzocyclobutene.
Benzocyclobutadiene
Names
Preferred IUPAC name Bicycloocta-1,3,5,7-tetraene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6HKey: WHEATZOONURNGF-UHFFFAOYSA-N
  • InChI=1/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6HKey: WHEATZOONURNGF-UHFFFAOYAK
SMILES
  • C12=CC=CC=C1C=C2
Properties
Chemical formula C8H6
Molar mass 102.136 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Benzocyclobutadiene is the simplest polycyclic hydrocarbon, being composed of an aromatic benzene ring fused to an anti-aromatic cyclobutadiene ring. It has chemical formula C8H6. Though the benzene ring is stabilized by aromaticity, the cyclobutadiene portion has a destabilizing effect. This results into it being a non-aromatic compound - neither behaving as aromatic nor an antiaromatic one. For this reason, benzocyclobutadiene will readily dimerize or polymerize and it reacts as a dienophile in Diels-Alder reactions.

Benzocyclobutadiene is used in the production of the pharmaceutical drug naflocort.

See also

References

  1. Observation of benzocyclobutadiene by flow nuclear magnetic resonance https://doi.org/10.1021/ja00168a059
  2. Carey, Francis A.; Sundberg, Richard J. (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York, NY: Plenum Press. ISBN 0-306-41198-9.
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