Benzocyclobutadiene

Benzocyclobutadiene
Names
	IUPAC name Bicyclo[4.2.0]octa-1,3,5,7-tetraene
Identifiers
CAS Number	4026-23-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	70373 ;
PubChem CID	77987;
CompTox Dashboard (EPA)	DTXSID60193245 ;
	InChI InChI=1S/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H Key: WHEATZOONURNGF-UHFFFAOYSA-N ; InChI=1/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H Key: WHEATZOONURNGF-UHFFFAOYAK;
	SMILES C12=CC=CC=C1C=C2;
Properties
Chemical formula	C8H6
Molar mass	102.136 g·mol−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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	Infobox references

Benzocyclobutadiene is the simplest polycyclic aromatic hydrocarbon, being composed of a benzene ring fused to a cyclobutadiene ring. It has chemical formula C₈H₆. Though the benzene ring is stabilized by aromaticity, the cyclobutadiene portion has a destabilizing effect. For this reason, benzocyclobutadiene will readily dimerize or polymerize and it reacts as a dienophile in Diels-Alder reactions.[1]

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

References

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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