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Benzocyclobutene

Benzocyclobutene

BCB Benzocyclobutene (not in accordance with IUPAC nomenclature)

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

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.

Derivatives

The benzocyclobutene moiety has also appeared in a number of chemical compounds with pharmacological properties such as ivabradine and S33005.

Additionally, cyclized phenethylamine psychedelic drugs containing the benzocyclobutene ring system, including TCB-2, tomscaline, bromotomscaline, and 2CBCB-NBOMe (NBOMe-TCB-2), have been described. A benzocyclobutene-derived amphetamine has been patented as well, and a benzocyclobutene containing designer drug, the substituted cathinone derivative 3,4-EtPV, has been sold in Europe. The benzocyclobutene derivative 2C-G-2 has also been claimed in a patent as an antiinflammatory, but no synthesis or activity data is provided so it is unclear if it has actually been made.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/164410 164410 Benzocyclobutene 98%]
  2. (2001). "Recent chemistry of benzocyclobutenes". Tetrahedron Lett..
  3. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
  4. "Substituted 7-aminoalkylbicyclo-[4. 2. 0]octa-1,3,5-trienes".
  5. (6 June 2025). "European Drug Report 2025 – Full Book". European Union Drugs Agency (euda.europa.eu).
  6. [https://patents.google.com/patent/WO2022271982A1/en Halpert M. Substituted phenethylamine for treating inflammation and psychological disorders. WO 2022/271982]
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