208-37-7

Basic information

• Product Name: BENZO[1,2-B:4,5-B']BISBENZOFURAN
• Synonyms: BENZO[1,2-B:4,5-B']BISBENZOFURAN
• CAS NO: 208-37-7
• Molecular Formula: C₁₈H₁₀O₂
• Molecular Weight: 258.27
• Mol File: 208-37-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 265.5-266.5 °C
• Boiling Point: 447.006 °C at 760 mmHg
• Flash Point: 244.747 °C
• Appearance: /
• Density: 1.349 g/cm³
• CAS DataBase Reference: BENZO[1,2-B:4,5-B']BISBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[1,2-B:4,5-B']BISBENZOFURAN(208-37-7)
• EPA Substance Registry System: BENZO[1,2-B:4,5-B']BISBENZOFURAN(208-37-7)

Safety Data

• Hazardous Substances Data: 208-37-7(Hazardous Substances Data)

Usage

General Description

Benzo[1,2-b:4,5-b']bisbenzofuran is a polycyclic aromatic hydrocarbon compound consisting of two benzofuran rings fused at the 1,2- and 4,5-positions. It is a highly aromatic and stable molecule that is often used as a chemical intermediate in the synthesis of organic compounds. Benzo[1,2-b:4,5-b']bisbenzofuran has been studied for its potential as a semiconductor material in the field of organic electronics, due to its unique electronic and optoelectronic properties. However, it is important to note that this compound may pose potential health hazards and environmental risks, and proper handling and disposal procedures should be followed when working with it.

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Relevant articles and documents

NMR and DFT studies on persistent carbocations derived from benzo[kl]xanthene, dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran, and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran in superacidic media

Persistent carbocations generated by the protonation of hetero-polycyclic aromatic compounds with oxygen atom(s) were studied by experimental NMR and density function theory calculations. Benzo[kl]xanthene (1), dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran (2), and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran (3) were synthesized by the annulation of arenediazonium salts. Compound 1 in FSO3H-SbF5 (4:1)/SO2ClF and 3 in FSO3H-SbF5 (1:1)/SO2ClF ionized to 1aH+ with protonation at C(4) and to 3aH+ with protonation at C(6), and these cations were successfully observed by NMR at low temperatures. The density function theory calculations indicated that 1aH+ and 3aH+ were the most stable protonated carbocations and that 2 should ionize to 2aH+ with protonation at C(6). According to the changes in 13C chemical shifts (Δδ13C), the positive charge was delocalized into the naphthalene unit for 1aH+, into one benzo[b,d]furan unit for 2aH+, and into one benzo[b,d]furan unit for 3aH+. The most stable persistent cations derived from the title compounds, 1-3, were found to be 1aH+ with protonation at C(4), 2aH+ with protonation at C(6), and 3aH+ with protonation at C(6) by experimental and theoretical methods.