Benzocyclobutene
| Skeletal formula | |
| Ball-and-stick model | |
| Names | |
|---|---|
| IUPAC name
Benzocyclobutene
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| Other names
BCB
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| Identifiers | |
694-87-1  |
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| ChEBI | CHEBI:87328  |
| ChemSpider | 62868 |
| Jmol 3D model | Interactive image |
| PubChem | 24850072 |
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| Properties | |
| C8H8 | |
| Molar mass | 104.15 g·mol−1 |
| Density | 0.957 g/cm3 |
| Boiling point | 150 °C (302 °F; 423 K) |
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Refractive index (nD)
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1.541 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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:[2]
Also see S33005 and the benzocyclobutene analog of 2-cb was prepared by Nichols et al.[3]
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
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- ↑ 164410 Benzocyclobutene 98%
- ↑ U.S. Patent 3,149,159
- ↑ http://www.bindingdb.org/data/mols/tenK5019/MolStructure_50194752.html
- ↑ Mehta, G.; Kotha, S. Recent chemistry of benzocyclobutenes. Tetrahedron Lett. 2001, 57.
