Benzocyclobutene

Benzocyclobutene

Benzocyclobutene

Chemical compound

Benzocyclobutene (BCB) is a benzene ring fused to a cyclobutane ring. It has chemical formula C8H8.[1]

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BCB is frequently used to create photosensitive polymers. BCB-based polymer dielectrics may be spun on or applied to various substrates for use in Micro Electro-Mechanical Systems (MEMS) and microelectronics processing. Applications include wafer bonding, optical interconnects, low-κ dielectrics, or even intracortical neural implants.

Reactions

Benzocyclobutene is a strained system which, upon heating to approximately 180 °C, causes the cyclobutene to undergo a conrotatory ring-opening reaction, forming o-xylylene. Since this process destroys the aromaticity of the benzene ring, the reverse reaction is highly favored.

Thermal generation of o-xylylene from benzocyclobutene

o-Xylylenes generated in this way have been used prolifically in cycloaddition reactions, which restore the aromaticity to the benzene ring, while forming a new annulated species.[2]

Uses

The benzocyclobutene moiety has also appeared in a number of chemical compounds with pharmacological properties such as ivabradine and S33005. Additionally, the benzocyclobutene analog of 2C-B has been prepared[3] and a benzocyclobutene-derived amphetamine has been patented.[4]

See also

References

  1. [1]
    164410 Benzocyclobutene 98%
  2. [2]
    Mehta, G.; Kotha, S. (2001). "Recent chemistry of benzocyclobutenes" (PDF). Tetrahedron Lett. 57 (4): 625–659. doi:10.1016/s0040-4020(00)00958-3.
  3. [3]
    "The Binding Database".
  4. [4]
    US 3149159, "Substituted 7-aminoalkylbicyclo-[4. 2. 0]octa-1,3,5-trienes"
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