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Benzocyclobutene

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Benzocyclobutene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Bicycloocta-1,3,5-triene
Other names Benzocyclobutane
BCB
Benzocyclobutene (not in accordance with IUPAC nomenclature)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.161.355 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2Key: UMIVXZPTRXBADB-UHFFFAOYSA-N
  • InChI=1/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2Key: UMIVXZPTRXBADB-UHFFFAOYAR
SMILES
  • C12=CC=CC=C1CC2
Properties
Chemical formula C8H8
Molar mass 104.152 g·mol
Density 0.957 g/cm
Boiling point 150 °C (302 °F; 423 K)
Refractive index (nD) 1.541
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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
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.

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 and a benzocyclobutene-derived amphetamine has been patented.

See also

References

  1. 164410 Benzocyclobutene 98%
  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. "The Binding Database".
  4. US 3149159, "Substituted 7-aminoalkylbicyclo-octa-1,3,5-trienes" 
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