Barrelene

Barrelene
Names
	Preferred IUPAC name Bicyclo[2.2.2]octa-2,5,7-triene
Identifiers
CAS Number	500-24-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	120100 ;
PubChem CID	136326;
UNII	2P5L4Z7K7I;
CompTox Dashboard (EPA)	DTXSID80198171 ;
	InChI InChI=1S/C8H8/c1-2-8-5-3-7(1)4-6-8/h1-8H Key: RHCCUQVVABYRDN-UHFFFAOYSA-N ; InChI=1/C8H8/c1-2-8-5-3-7(1)4-6-8/h1-8H Key: RHCCUQVVABYRDN-UHFFFAOYAN;
	SMILES C1(C=C2)C=CC2C=C1; C\1=C\C\2/C=C\C/1/C=C/2;
Properties
Chemical formula	C8H8
Molar mass	104.15
Density	1.013 g/mL
Boiling point	153.7 °C (308.7 °F; 426.8 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Barrelene is a bicyclic organic compound with chemical formula C₈H₈ and systematic name bicyclo[2.2.2]octa-2,5,7-triene. First synthesized and described by Howard Zimmerman in 1960, the name derives from the resemblance to a barrel, with the staves being three ethylene units attached to two methine groups. It is the formal Diels–Alder adduct of benzene and acetylene. Due to its unusual molecular geometry, the compound is of considerable interest to theoretical chemists.

Iptycenes, with the alkene groups part of an arenes, are related compounds. It is also a starting material for many other organic compounds, such as semibullvalene.