109811-96-3

Basic information

• Product Name: 1H-Indole, 1-methyl-3-(2-nitro-1-phenylethyl)-
• CAS NO: 109811-96-3
• Molecular Formula: C17H16N2O2
• Molecular Weight: 280.326
• Mol File: 109811-96-3.mol
• Article Data: 74

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 1-methyl-3-(2-nitro-1-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 1-methyl-3-(2-nitro-1-phenylethyl)-(109811-96-3)
• EPA Substance Registry System: 1H-Indole, 1-methyl-3-(2-nitro-1-phenylethyl)-(109811-96-3)

Safety Data

• Hazardous Substances Data: 109811-96-3(Hazardous Substances Data)

Upstream product

• 5153-67-3 nitrostyrene 
• 158953-96-9 1-methyl-3-deuterio-1H-indole 
• 100-42-5 styrene 
• 603-76-9 1-methylindole 
• 102-96-5 (2-nitroethenyl)benzene 

Downstream Products

• 102889-07-6 2-(1-methyl-1H-indol-3-yl)-2-phenylethan-1-amine 

Relevant articles and documents

Structural considerations for charge-enhanced Br?nsted acid catalysts

All three N-methylated and N-protonated hydroxypyridinium BArF4– salt isomers were synthesized and their hydrogen bond donating abilities were investigated. DFT and G4 theory computations along with IR spectroscopic measurements were found to be effective methods for predicting the catalytic activities of these O–H and N–H Br?nsted acids. A UV-vis titration approach for rapidly quantifying hydrogen bond donating ability revealed that carbon-hydrogen bonds also can participate in electrostatic interactions, but the presence of multiple equilibrium complexes results in a limitation of this method. In the methylated series of hydroxypyridines, the ortho and para isomers displayed modest rate enhancements relative to the meta derivative. Protonation introduces a new acidic site and the ortho hydroxypyridinium ion salt is a significantly more active catalyst than all of the other species examined. This is indicative of bidentate activation by the N–H and O–H acidic sites, and suggests a new design strategy for improving charge-enhanced catalysts.

Cooperative hydrogen-bonding effects in silanediol catalysis

The importance of cooperative hydrogen-bonding effects and SiOH-acidification is described for silanediol catalysis. NMR binding, X-ray, and computational studies provide support for a unique dimer resulting from silanediol self-recognition. The significa

Strategic Stereoselective Halogen (F, Cl) Insertion: A Tool to Enhance Supramolecular Properties in Polyols

To improve the supramolecular properties of organic compounds, chemists continuously need to identify new tools. Herein, the influence of the stereoselective insertion of halogen atoms (F or Cl) on different supramolecular properties is analyzed. Insertin

Electrostatically Enhanced Thioureas

A new class of readily prepared thiourea catalysts with one or more positively charged centers and no new hydrogen-bonding sites are exploited in several bond-forming reactions and are orders of magnitude more reactive than Schreiner's thiourea. These fin

Efficient iron-catalyzed Michael addition of indole to nitroolefins under solvent-free conditions

Iron trichloride hexahydrate has proved to be an effective catalyst for Michael addition of indole to nitroolefins under solvent-free conditions to produce the corresponding adducts with appreciable yields. Graphical Abstract: Solvent-free Michael additio

1-Dodecyloxy-4-perfluoroalkylbenzene as a Novel Efficient Additive in Aldol Reactions and Friedel-Crafts Alkylation in Supercritical Carbon Dioxide

matrix presented 1-Dodecyloxy-4-perfluoroalkylbenzenes accelerated organic reactions such as aldol-type reactions and Friedel-Crafts alkylation in supercritical carbon dioxide. The perfluoroalkylbenzene worked as a surfactant in the system, and formation of emulsions during the reactions was observed.

The combined use of cationic palladium(II) with a surfactant for the C-H functionalization of indoles and pyrroles in water

The utility of electrophilic palladium(II) species was demonstrated for C-H bond functionalization of indoles and pyrroles in water. The system displayed attractive features that are reminiscent of both precious-metal catalysis and micellar catalysis.

A robust heterogeneous Co-MOF catalyst in azide-alkyne cycloaddition and Friedel-Crafts reactions as well as hydrosilylation of alkynes

Organic reactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmentally friendly features and potential catalyst recyclability. A robust Co(ii)-MOF {[Co2(l-mac)(4,4-bpt)(H2O)]·3.5H2O}n (1) and its enantiomer {[Co2(d-mac)(4,4-bpt)(H2O)]·3.5H2O}n (2) (l/d-mac = basic forms of l/d-malic acid, 4,4-Hbpt = 3,5-di(pyridin-4-yl)-4H-1,2,4-triazole) have been gram-scale prepared under solvothermal conditions. Structural analysis reveals that mac manages Co(ii) ions to form 1-D chains, which are further extended via 4,4-bpt connectors into a noninterpenetrating 3D framework architecture. It was found that 1 can be as a heterogeneous catalyst for multiple organic reactions, such as azide-alkyne cycloaddition and Friedel-Crafts reactions with good isolated yields and good recycle runs (at least five times without substantial degradation). Additionally, 1 can promote hydrosilylation of alkynes under harsh conditions with moderate yield. This journal is

Rose bengal as photocatalyst: Visible light-mediated Friedel-Crafts alkylation of indoles with nitroalkenes in water

A novel and facile visible-light-mediated alkylation of indoles and nitroalkenes has been developed. In this protocol, rose bengal acts as a photosensitizer, and environmentally benign water was used as the green and efficient reaction medium. Indoles rea