Benzocyclobutene

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Benzocyclobutene
Benzocyclobutene.png
Benzocyclobutene-3D-balls.png
Names
Preferred IUPAC name
Bicyclo[4.2.0]octa-1,3,5-triene
Other names
Benzocyclobutane
BCB
Benzocyclobutene (not in accordance with IUPAC nomenclature)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.161.355 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2 X mark.svgN
    Key: UMIVXZPTRXBADB-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
    Key: UMIVXZPTRXBADB-UHFFFAOYAR
  • C12=CC=CC=C1CC2
Properties
C8H8
Molar mass 104.152 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).
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Infobox references

Benzocyclobutene (BCB) is a benzene ring fused to a cyclobutane ring. It has chemical formula C 8 H 8. [1]

Contents

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.

Thermal generation of o-xylylene from benzocyclobutene Thermolytic ring-opening reaction of benzocyclobutene generating o-xylylene.png
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

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 [3] and a benzocyclobutene-derived amphetamine has been patented. [4]

See also

Related Research Articles

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Petrochemical Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

Naphthalene Chemical compound

Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.

Aromaticity Phenomenon providing chemical stability in resonating hybrids of cyclic organic compounds

In chemistry, aromaticity is a property of cyclic (ring-shaped), typically planar (flat) molecular structures with pi bonds in resonance that gives increased stability compared to other geometric or connective arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability.

Aniline Chemical compound

Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.

Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O) selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.

An alkyne trimerisation reaction is a [2+2+2] cycloaddition reaction in which three alkyne units react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles.

Cyclooctatetraene Chemical compound

1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as [8]annulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy.

Nucleophilic aromatic substitution Chemical reaction mechanism

A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution. Just as normally nucleophilic alkenes can be made to undergo conjugate substitution if they carry electron-withdrawing substituents, so normally nucleophilic aromatic rings also become electrophilic if they have the right substituents.

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Cyclic compound Molecule with a ring of bonded atoms

A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.

Parylene

Parylene is the common name of a polymer whose backbone consists of para-benzenediyl rings –C
6
H
4
– connected by 1,2-ethanediyl bridges –CH
2
CH
2
–. It can be obtained by polymerization of para-xylyleneH
2
C
=C
6
H
4
=CH
2
.

Fluorobenzene Chemical compound

Fluorobenzene is the chemical compound with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds.

Adhesive bonding describes a wafer bonding technique with applying an intermediate layer to connect substrates of different types of materials. Those connections produced can be soluble or insoluble. The commercially available adhesive can be organic or inorganic and is deposited on one or both substrate surfaces. Adhesives, especially the well-established SU-8, and benzocyclobutene (BCB), are specialized for MEMS or electronic component production.

Superphane Chemical compound

[2.2.2.2.2.2]( 1,2,3,4,5,6)Cyclophane or superphane is a 6-fold bridged cyclophane with all arene positions in the benzene dimer taken up by ethylene spacers. The compound has been of some scientific interest as a model for testing aromaticity and was first synthesised by Virgil Boekelheide in 1979. Superphane is the base compound for a large group of derivatives with structural variations. The analogs with 2 to 5 bridges are also known compounds. The benzene rings have been replaced by other aromatic units, such as those based on ferrocene or stabilized cyclobutadiene. Numerous derivatives are known with variations in the type and length of the bridging units.

Quelet reaction

The Quelet reaction is an organic coupling reaction in which a phenolic ether reacts with an aliphatic aldehyde to generate an α-chloroalkyl derivative. The Quelet reaction is an example of a larger class of reaction, electrophilic aromatic substitution. The reaction is named after its creator R. Quelet, who first reported the reaction in 1932, and is similar to the Blanc chloromethylation process.

Xylylene

Xylylene (sometimes quinone-dimethides) comprises two isomeric organic compounds with the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, an example being tetracyanoquinodimethane.

The chemical compound xylylene dichloride (C6H4(CH2Cl)2) is a white to light yellow sandlike solid. This compound can be classified as a benzyl halide. Xylylene dichloride is used as a vulcanizing agent to harden rubbers. It catalyzes the crosslinking of phenolic resins.

References

  1. 164410 Benzocyclobutene 98%
  2. Mehta, G.; Kotha, S. (2001). "Recent chemistry of benzocyclobutenes" (PDF). Tetrahedron Lett. 57 (4): 625–659. doi:10.1016/s0040-4020(00)00958-3.
  3. "The Binding Database".
  4. US 3149159,"Substituted 7-aminoalkylbicyclo-[4. 2. 0]octa-1,3,5-trienes"