24253-53-0

Basic information

• Product Name: 2,11-diphenyltriphenylene
• Synonyms: 2,11-diphenyltriphenylene
• CAS NO: 24253-53-0
• Molecular Weight: 380.489
• Mol File: 24253-53-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,11-diphenyltriphenylene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,11-diphenyltriphenylene(24253-53-0)
• EPA Substance Registry System: 2,11-diphenyltriphenylene(24253-53-0)

Safety Data

• Hazardous Substances Data: 24253-53-0(Hazardous Substances Data)

Upstream product

• 5943-11-3 2,8-diiodo-dibenzo[b,d]furan 
• 100-58-3 phenylmagnesium bromide 
• 58841-73-9 2,8-diphenyldibenzofuran 
• 591-50-4 iodobenzene 
• 5122-95-2 3-Biphenylboronic acid 
• 24253-44-9 4,4''-diiodo-o-terphenyl 
• 71-43-2 benzene 
• 5660-43-5 4,4''-diphenyl-o-terphenyl 
• 101228-48-2 2,8-diphenyl-dibenzo[b,d]thiophene 

Relevant articles and documents

Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation

A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.

Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes

Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.