51206-84-9

Basic information

• Product Name: 3-(4-nitrophenyl)-1H-indole
• CAS NO: 51206-84-9
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.2414
• Mol File: 51206-84-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 471.6°C at 760 mmHg
• Flash Point: 239°C
• Density: 1.33g/cm³
• Vapor Pressure: 1.3E-08mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: 3-(4-nitrophenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-nitrophenyl)-1H-indole(51206-84-9)
• EPA Substance Registry System: 3-(4-nitrophenyl)-1H-indole(51206-84-9)

Safety Data

• Hazardous Substances Data: 51206-84-9(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 100-01-6 4-nitro-aniline 
• 98-95-3 nitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 771-50-6 1H-indole-3-carboxylic acid 
• 62-53-3 aniline 
• 100-13-0 4-nitrostyrene 
• 68-34-8 phenyl toluenesulfonamide 

Relevant articles and documents

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.

Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands

The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).

Metal-free, C-H arylation of indole and its derivatives with aryl diazonium salts by visible-light photoredox catalysis

In this Letter, we present the Rhodamine B catalyzed direct C-H arylation of indole with aryl diazonium salts. This method only requires green light and room temperature.