Biphenylene

Biphenylene
IUPAC name Biphenylene
Other names Diphenylene
Identifiers
CAS number	259-79-0 Y
Properties
Molecular formula	C12H8
Molar mass	152.19 g/mol
Appearance	solid
Melting point	109 - 111 °C
Related compounds
Related unsaturated hydrocarbons	benzene cyclobutene cyclobutadiene
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Biphenylene is a compound composed of two aryl rings fused together to form a 6-4-6 arene system. The structure appears to be planar, which is concerted by its antiaromaticity ^[1]

Biphenylene is probably best known as the dimer of benzyne, which serves as one synthetic route.

References

1. ^ Waser, Jurg; Lu, Chia-Si (1944). "The Crystal Structure of Biphenylene". J. Am. Chem. Soc 66 (12): 2035–2042. doi:10.1021/ja01240a012.