112817-88-6

Basic information

• Product Name: 1H-Indole, 3-methyl-1-phenyl-
• CAS NO: 112817-88-6
• Molecular Formula: C15H13N
• Molecular Weight: 207.275
• Mol File: 112817-88-6.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-methyl-1-phenyl-(112817-88-6)
• EPA Substance Registry System: 1H-Indole, 3-methyl-1-phenyl-(112817-88-6)

Safety Data

• Hazardous Substances Data: 112817-88-6(Hazardous Substances Data)

Upstream product

• 123-38-6 propionaldehyde 
• 530-50-7 1,1-Diphenylhydrazine 
• 62-53-3 aniline 
• 68913-15-5 (Z)-1-chloro-2-(2-chloro-1-methylvinyl)benzene 
• 68913-16-6 (E)-1-chloro-2-(2-chloro-1-methylvinyl)benzene 
• 83-34-1 3-Methylindole 
• 462-06-6 fluorobenzene 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 108-90-7 chlorobenzene 
• 337966-00-4 2-(ortho-bromophenyl)-2-methyl-ethylamine 
• 52562-19-3 2-isopropenylaniline 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 1262588-64-6 2-(3-methoxyphenyl)-3-methyl-1-phenylindole 
• 1616246-75-3 N-methyl-N-(3-methyl-1-phenyl-1H-indol-2-yl)benzenesulfonamide 
• 23210-22-2 1-Phenyl-3-methylindolin-2-one 
• 138349-55-0 4-chloro-N-(3-methyl-1-phenyl-1H-indol-2-yl)benzamide 
• 1311205-16-9 3-methyl-1-phenyl-2-(trifluoromethyl)-1H-indole 
• 16176-77-5 2-methyl-1-phenyl-1H-indole 
• 92552-17-5 10-Methyl-5H-dibenzoazepine 
• 6267-02-3 9,9‐dimethyl‐10H‐acridine 

Relevant articles and documents

A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water

A polymer-anchored Cu(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermogravimetric analysis (TGA). This heterogeneous Cu(II) catalyst, efficiently works for the N-arylation of indoles and Sonogashira coupling of terminal alkynes with aryl halides in aqueous medium. The effect of solvent, and base for the C-N, and C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to four times without significant loss of its catalytic activity.

Aqueous copper-catalyzed N-arylation of indoles: The surfactant strategy

Surfactants have long been underestimated in synthetic organic chemistry despite their great potential in promoting solubility, reactivity and selectivity in metal-mediated cross-couplings. In this study the strategy of surfactant promotion was exemplified in copper-catalyzed N-arylation of indoles in water. The different effects of surfactants during the coupling reaction were first explored. The superior promoting effect of the natural zwitterionic surfactant, betaine, was found and attributed to the capability of the formed complex to stabilize the copper intermediate in the catalytic transformation and facilitate transportation of the reactants. The concept of surfactant promotion through complexation is valuable in metal-mediated cross-couplings. This method also exhibited good recycling ability. This study will greatly facilitate exploration of surfactant promotion in metal-mediated cross-couplings.

COPPER CATALYSED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS TRIFLUOROACETATE

Indoles are C(3)- or N-phenylated by triphenylbismuth bis-fluoroacetate under copper catalysis.C(3)-Phenyl derivatives are obtained with C(3)-unsubstituted indoles and N-phenyl derivatives with C(3)-substituted indoles.

L-Arginine as a base and ligand for the palladium-catalyzed C-C and C-N cross-coupling reactions in aqueous media

L-Arginine (2-amino-5-guanidinopentanoic acid) acts as a base and ligand in reaction medium, exhibits a very high activity and recyclability to palladium-catalyzed C-C and C-N cross-coupling reactions in aqueous media. The corresponding Suzuki products were obtained in good to excellent yields by using various aryl halides (I, Br, Cl). Also, the cross coupling reactions of arylboronic acids with various amines in aqueous medium proceed in good to excellent yield under same conditions. Furthermore, the catalyst could be easily separated from the reaction mixture and could be recycled several times without significant loss in its catalytic activity.

Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates

A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.