Benzocyclobutene
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 442352986
| ImageFile = Benzocyclobutene.png
| ImageSize = 140
| ImageAlt = Skeletal formula
| ImageFile1 = Benzocyclobutene-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model
| PIN = Bicyclo[4.2.0]octa-1,3,5-triene
| OtherNames=Benzocyclobutane
BCB
Benzocyclobutene (not in accordance with IUPAC nomenclature)
|Section1={{Chembox Identifiers
| CASNo=694-87-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MF7U8F3YLB
| PubChem=69667
| SMILES=C12=CC=CC=C1CC2
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 62868
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 87328
| InChI = 1/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
| InChIKey = UMIVXZPTRXBADB-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UMIVXZPTRXBADB-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=8 | H=8
| Appearance=
| Density= 0.957 g/cm3
| MeltingPt=
| BoilingPtC=150
| Solubility=
| RefractIndex = 1.541
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
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Benzocyclobutene (BCB) is a benzene ring fused to a cyclobutane ring. It has chemical formula {{chem2|auto=1|C8H8}}.[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/164410 164410 Benzocyclobutene 98%]
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.
File:Thermolytic ring-opening reaction of benzocyclobutene generating o-xylylene.png
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.{{cite journal |author1=Mehta, G. |author2=Kotha, S. | title = Recent chemistry of benzocyclobutenes |journal = Tetrahedron Lett. |volume=57 |issue=4 | date = 2001 | pages = 625–659 | doi = 10.1016/s0040-4020(00)00958-3 |url=http://eprints.iisc.ac.in/2691/1/01-SRK-Tetra-625.pdf }}
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{{cite web | url = http://www.bindingdb.org/data/mols/tenK5019/MolStructure_50194752.html | title = The Binding Database}} and a benzocyclobutene-derived amphetamine has been patented.{{Cite patent | title = Substituted 7-aminoalkylbicyclo-[4. 2. 0]octa-1,3,5-trienes | country = US | number = 3149159}}