250643-76-6

Basic information

• Product Name: Indium, tris(phenylethynyl)-
• CAS NO: 250643-76-6
• Molecular Formula: C24H15In
• Molecular Weight: 418.203
• Mol File: 250643-76-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Indium, tris(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Indium, tris(phenylethynyl)-(250643-76-6)
• EPA Substance Registry System: Indium, tris(phenylethynyl)-(250643-76-6)

Safety Data

• Hazardous Substances Data: 250643-76-6(Hazardous Substances Data)

Upstream product

• 10025-82-8 indium(III) chloride 
• 4440-01-1 lithium phenylacetylide 
• 536-74-3 phenylacetylene 
• 6738-06-3 phenylethynylmagnesium bromide 

Downstream Products

• 17684-06-9 1-phenyl-5-methyl-4-hexen-1-yn-3-one 
• 4980-70-5 1,3-diphenyl-1-propyne 
• 1942-31-0 4-(phenylethinyl)acetophenone 
• 83965-72-4 2,6-bis(2-phenylethynyl)pyridine 
• 90267-18-8 2,5-bis(phenylethynyl)thiophene 
• 118688-56-5 1,3,5-tris(2-phenylethynyl)benzene 
• 15784-39-1 4-(phenylethynyl)-1,1'-biphenyl 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 13667-12-4 1-bromo-4-phenylethynylbenzene 
• 41304-88-5 1,1′-(1,4-phenylene) bis(3-phenylprop-2-yn-1-one) 
• 73969-16-1 (4E)-1-phenyl-5,9-dimethyl-4,8-decadien-1-yne 
• 1159987-65-1 C₂₆H₂₅NO₂ 
• 1159987-66-2 C₂₀H₂₀ClNO₂ 
• 1159987-67-3 C₂₀H₂₀ClNO₂ 

Relevant articles and documents

Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.

A phosphine-free, atom-efficient cross-coupling of aryl iodides with triarylindiums or trialkynylindiums catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous atom-efficient cross-coupling reaction of aryl iodides with triarylindiums or trialkynylindiums was achieved in THF at 68 °C by using 1 mol% of MCM-41-immobilized palladium(0)-Schiff base complex [MCM-41-N,N-Pd(0)] as catalyst, yielding a variety of unsymmetrical biaryls and arylalkynes in good to excellent yields. The heterogeneous palladium(0) catalyst could easily be prepared via a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution and recycled at least 10 times without significant loss of activity.

Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions with indium organometallics: Synthesis and photochemical studies

The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R3In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R3In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process.