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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 399919424 |
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| Watchedfields = changed |
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|ImageFile=Benzocyclobutene.png |
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| verifiedrevid = 442352986 |
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|ImageSize=150px |
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|IUPACName=Benzocyclobutene |
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| ImageFile = Benzocyclobutene.png |
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| ImageSize = 140 |
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|OtherNames=BCB |
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| ImageAlt = Skeletal formula |
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|Section1= {{Chembox Identifiers |
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| ImageFile1 = Benzocyclobutene-3D-balls.png |
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| ImageSize1 = 160 |
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| ImageAlt1 = Ball-and-stick model |
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| PIN = Bicycloocta-1,3,5-triene |
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| OtherNames=Benzocyclobutane<br />BCB<br />Benzocyclobutene (not in accordance with IUPAC nomenclature) |
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|Section1={{Chembox Identifiers |
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| CASNo=694-87-1 |
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| CASNo=694-87-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem=24850072 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = MF7U8F3YLB |
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| PubChem=69667 |
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| SMILES=C12=CC=CC=C1CC2 |
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| SMILES=C12=CC=CC=C1CC2 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 62868 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 87328 |
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| InChI = 1/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2 |
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| InChIKey = UMIVXZPTRXBADB-UHFFFAOYAR |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UMIVXZPTRXBADB-UHFFFAOYSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8|H=8 |
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| C=8 | H=8 |
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| Appearance= |
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| Density= 0.957 g/cm<sup>3</sup> |
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| Density= 0.957 g/cm<sup>3</sup> |
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| RefractIndex = 1.541 |
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| RefractIndex = 1.541 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Benzocyclobutene''' ('''BCB''') is a ] ring fused to a ] ring. It has ] {{carbon}}<sub>8</sub>{{hydrogen}}<sub>8</sub>.<ref></ref> |
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'''Benzocyclobutene''' ('''BCB''') is a ] ring fused to a ] ring. It has ] {{chem2|auto=1|C8H8}}.<ref></ref> |
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BCB is frequently used to create ] ]s. BCB-based polymer ]s may be spun on or applied to various ]s for use in ] (MEMS) and microelectronics processing. Applications include wafer bonding, optical interconnects, low-K dielectrics, or even intracortical ]s. |
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BCB is frequently used to create ] ]s. BCB-based polymer ]s may be spun on or applied to various ]s for use in ] (MEMS) and microelectronics processing. Applications include wafer bonding, optical interconnects, ]s, or even intracortical ]s. |
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==Reactions== |
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Benzocyclobutene is a strained system which, upon heating to approximately 180 °C, causes the cyclobutene to undergo a ] ], forming ]. Since this process destroys the ] of the benzene ring, the reverse reaction is highly favored. |
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] |
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''o''-Xylylenes generated in this way have been used prolifically in ]s, which restore the aromaticity to the benzene ring, while forming a new ] species.<ref>{{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 }}</ref> |
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==Uses== |
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The benzocyclobutene moiety has also appeared in a number of chemical compounds with pharmacological properties such as ] and ]. Additionally, the benzocyclobutene ] of ] has been prepared<ref>{{cite web | url = http://www.bindingdb.org/data/mols/tenK5019/MolStructure_50194752.html | title = The Binding Database}}</ref> and a benzocyclobutene-derived ] has been patented.<ref>{{Cite patent | title = Substituted 7-aminoalkylbicyclo-octa-1,3,5-trienes | country = US | number = 3149159}}</ref> |
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== See also == |
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== See also == |
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{{hydrocarbon-stub}} |
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