 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Bicyclo[4.2.0]octa-1,3,5-triene | |
| Other names Benzocyclobutane BCB Benzocyclobutene (not in accordance with IUPAC nomenclature) | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.161.355 |
| UNII | |
| |
| |
| Properties | |
| C8H8 | |
| Molar mass | 104.152 g·mol−1 |
| Density | 0.957 g/cm3 |
| Boiling point | 150 °C (302 °F; 423 K) |
Refractive index (nD) | 1.541 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Benzocyclobutene (BCB) is abenzene ring fused to acyclobutane ring. It haschemical formulaC8H8.[1]
BCB is frequently used to createphotosensitivepolymers. BCB-based polymerdielectrics may be spun on or applied to varioussubstrates for use inMicro Electro-Mechanical Systems (MEMS) and microelectronics processing. Applications include wafer bonding, optical interconnects,low-κ dielectrics, or even intracorticalneural implants.
Benzocyclobutene is a strained system which, upon heating to approximately 180 °C, causes the cyclobutene to undergo aconrotatoryring-opening reaction, formingo-xylylene. Since this process destroys thearomaticity of the benzene ring, the reverse reaction is highly favored.
o-Xylylenes generated in this way have been used prolifically incycloaddition reactions, which restore the aromaticity to the benzene ring, while forming a newannulated species.[2]
The benzocyclobutene moiety has also appeared in a number of chemical compounds with pharmacological properties such asivabradine andS33005. Additionally, the benzocyclobuteneanalog of2C-B has been prepared[3] and a benzocyclobutene-derivedamphetamine has been patented.[4]
