Benzocyclobutene

Benzocyclobutene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Benzocyclobutene
Other names
BCB
Identifiers
694-87-1 YesY
ChEBI CHEBI:87328 N
ChemSpider 62868 N
Jmol 3D model Interactive image
PubChem 24850072
Properties
C8H8
Molar mass 104.15 g·mol−1
Density 0.957 g/cm3
Boiling point 150 °C (302 °F; 423 K)
1.541
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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

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-K dielectrics, or even intracortical neural implants.

Pharmaceuticals

The Benzocyclobutene moiety has also appeared in a number of drug molecules. As an example, the amphetamine derived compound appears in the following patent: Substituted 7-aminoalkylbicyclo-[4. 2. 0] octa-1, 3, 5-trienes.[2]

Also see S33005 and the benzocyclobutene analog of 2-cb was prepared by Nichols et al.[3]

One known use of Benzocyclobutadiene was in the production of naflocort.

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 favoured.

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.[4]

See also

References

  1. ↑ 164410 Benzocyclobutene 98%
  2. ↑ U.S. Patent 3,149,159
  3. ↑ http://www.bindingdb.org/data/mols/tenK5019/MolStructure_50194752.html
  4. ↑ Mehta, G.; Kotha, S. Recent chemistry of benzocyclobutenes. Tetrahedron Lett. 2001, 57.
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