37654-32-3

Basic information

• Product Name: 2,2'-bitriphenylene
• Synonyms: 2,2'-bitriphenylene;2,2'-Bistriphenylyl
• CAS NO: 37654-32-3
• Molecular Formula: C₃₆H₂₂
• Molecular Weight: 454.55988
• Mol File: 37654-32-3.mol

Chemical Properties

• Melting Point: 356℃
• Appearance: /
• CAS DataBase Reference: 2,2'-bitriphenylene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-bitriphenylene(37654-32-3)
• EPA Substance Registry System: 2,2'-bitriphenylene(37654-32-3)

Safety Data

• Hazardous Substances Data: 37654-32-3(Hazardous Substances Data)

Usage

General Description

2,2'-Bitriphenylene is a chemical compound that belongs to the family of polycyclic aromatic hydrocarbons. It is a colorless crystalline solid at room temperature and is insoluble in water. It is primarily used as a building block in the synthesis of various organic compounds, including dyes, pigments, and pharmaceuticals. 2,2'-Bitriphenylene is also under research for its potential use in organic electronics and as a precursor for the production of carbon-based materials such as graphene. However,

Upstream product

• 84-15-1 o-terphenyl 
• 24253-48-3 2-methoxytriphenylene 
• 19111-87-6 2-bromobenzo[9,10]phenanthrene 

Relevant articles and documents

Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant

Nickel-catalyzed reductive homocoupling of aryl ethers has been achieved with Mg(anthracene)(thf) 3as a readily available low-cost reductant. DFT calculations provided a rationale for the specific efficiency of the diorganomagnesium-type two-electron reducing agent. The calculations show that the dianionic anthracene-9,10-diyl ligand reduces the two aryl ether substrates, resulting in the homocoupling reaction through supply of electrons to the Ni-Mg bimetallic system to form organomagnesium nickel(0)-ate complexes, which cause two sequential C-O bond cleavage reactions. The calculations also showed cooperative actions of Lewis acidic magnesium atoms and electron-rich nickel atoms in the C-O cleavage reactions.

Controlling the Scholl reaction

Guidelines for the application of the Scholl reaction were developed. Labeling experiments demonstrate that the Scholl reaction fails in small, unsubstituted oligophenylenes (e.g., o-terphenyl) due to oligomerization of the products (e.g., triphenylene). Incorporation of suitably placed blocking groups (e.g., t-butyl) suppresses oligomerization. The well-established directing group effects in electrophilic aromatic substitution predict the outcome of Scholl reactions of substituted substrates. Activating o,p-directing groups (e.g., MeO) direct bond formation o,p, either intramolecularly or intermolecularly. Deactivating o,p-directing groups (e.g., Br) also direct bond formation o,p but yields are lower. Deactivating m-directors (e.g., NO2) suppress reaction. MoCl5 and PhI(OOCCF3)2/BF 3·Et2O are general and effective reagents for the Scholl oxidation. Calculations (B3LYP/6-31G(d)) predict the Scholl reaction in alkoxyarenes to proceed via arenium cations, not radical cations. Suzuki-Miyaura couplings were used to generate 12 substituted o-terphenyl derivatives.