Benzocyclobutene

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| 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

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| RefractIndex = 1.541

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|Section3={{Chembox Hazards

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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}}

See also

References