Benzocyclobutene

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Benzocyclobutene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Benzocyclobutene
Other names
BCB
Identifiers
694-87-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:87328 N
ChemSpider 62868 N
ECHA InfoCard 100.161.355
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.

Reactions[edit]

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.

Thermal generation of o-xylylene from benzocyclobutene

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.[2]

Uses[edit]

The benzocyclobutene moiety has also appeared in a number of chemical compounds with pharmacological properties such as ivabradine and S33005. Additionallly, the benzocyclobutene analog of 2C-B has been prepared[3] and a benzocyclobutene-derived amphetamine has been patented.[4]

See also[edit]

References[edit]

  1. ^ 164410 Benzocyclobutene 98%
  2. ^ Mehta, G.; Kotha, S. (2001). "Recent chemistry of benzocyclobutenes". Tetrahedron Lett.: 57. 
  3. ^ "The Binding Database". 
  4. ^ US 3149159, "Substituted 7-aminoalkylbicyclo-[4. 2. 0]octa-1,3,5-trienes"