Description

Benzocyclobutene (CAS: 694-87-1) is a highly reactive organic compound with the molecular formula C₈H₈ and IUPAC name bicyclo[4.2.0]octa-1,3,5-triene. This strained bicyclic hydrocarbon features a fused benzene and cyclobutene ring system, making it a valuable intermediate in synthetic organic chemistry and materials science. Its unique structure imparts significant ring strain, leading to interesting thermal and chemical reactivity, particularly in polymerization and Diels-Alder reactions. Benzocyclobutene is widely utilized in the development of advanced polymers, photoresists, and low-dielectric-constant materials for microelectronics. Available in high purity grades, this compound is essential for researchers working on thermally stable polymers, semiconductor coatings, and crosslinking agents. Store under inert conditions to maintain stability.

Properties

• CAS Number: 694-87-1
• Complexity: 74
• IUPAC Name: bicyclo[4.2.0]octa-1,3,5-triene
• InChI: InChI=1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
• InChI Key: UMIVXZPTRXBADB-UHFFFAOYSA-N
• Exact Mass: 104.062600255
• Molecular Formula: C8H8
• Molecular Weight: 104.15
• SMILES: C1CC2=CC=CC=C21
• Monoisotopic Mass: 104.062600255
• Physical Description: Colorless liquid;
• Synonyms: Benzocyclobutene, Bicyclo[4.2.0]octa-1,3,5-triene, Benzocyclobutane, Bicyclo(4.2.0)octa-1,3,5-triene, MF7U8F3YLB, 1,2-dihydrocyclobutabenzene, 1,2-Dihydrobenzocyclobutene, Benzocyclobutene, 1,2-dihydro-, DTXSID3073927, CHEBI:87328, BICYCLO(4.2.0)OCTA-2,4,6-TRIENE, DTXCID1046502, DTXCID70115736, Bicyclo(4.2.0)octa1,3,5,7tetraene, 4026-23-7, dtxsid60193245, inchi=1/c8h8/c1-2-4-8-6-5-7(8)3-1/h1-4h,5-6h, umivxzptrxbadb-uhfffaoysa-n, un3295, 694-87-1, MFCD01321219, cyclobutabenzene, C8H8, Benzocyclobutene, 98%, UNII-MF7U8F3YLB, SCHEMBL8700, SCHEMBL33555, SCHEMBL34906, SCHEMBL34907, SCHEMBL2144679, SCHEMBL3979789, SCHEMBL9630603, STL452965, AKOS004907664, CS-W016636, DS-4372, FB57841, SY052978, bicyclo[4.2.0]octa-1(6),2,4-triene, B3863, EN300-104400, F15000, Q420972

Application

Benzocyclobutene is primarily used as a precursor in the synthesis of high-performance polymers and resins with exceptional thermal and mechanical properties. Its strained ring system enables efficient crosslinking reactions, making it valuable in the production of low-k dielectric materials for semiconductor applications. Researchers also employ benzocyclobutene derivatives as photoactive compounds in advanced photoresist formulations for microfabrication.

Safety and Hazards

GHS Hazard Statements

• H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
• H332 (31%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H412 (31%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (100%)
• Acute Tox. 4 (31%)
• Aquatic Chronic 3 (31%)

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