31951-33-4

Usage

InChI:InChI=1/C10H9NO/c1-8-6-11(7-12)10-5-3-2-4-9(8)10/h2-7H,1H3

Upstream product

• 83-34-1 3-Methylindole 
• 64-18-6 formic acid 
• 1478-41-7 diethoxycarbonium fluoroborate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 89725-80-4 3-Methyl-indole-1-carbaldehyde oxime 
• 83836-39-9 N-[1-(3-Methyl-indol-1-yl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

Molecularly Defined Manganese Catalyst for Low-Temperature Hydrogenation of Carbon Monoxide to Methanol

Methanol synthesis from syngas (CO/H2 mixtures) is one of the largest manmade chemical processes with annual production reaching 100 million tons. The current industrial method proceeds at high temperatures (200-300 °C) and pressures (50-100 atm) using a copper-zinc-based heterogeneous catalyst. In contrast, here, we report a molecularly defined manganese catalyst that allows for low-temperature/low-pressure (120-150 °C, 50 bar) carbon monoxide hydrogenation to methanol. This new approach was evaluated and optimized by quantum mechanical simulations virtual high-throughput screenings. Crucial for this achievement is the use of amine-based promoters, which capture carbon monoxide to give formamide intermediates, which then undergo manganese-catalyzed hydrogenolysis, regenerating the promoter. Following this conceptually new approach, high selectivity toward methanol and catalyst turnover numbers (up to 3170) was achieved. The proposed general catalytic cycle for methanol synthesis is supported by model studies and detailed spectroscopic investigations.

Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: A novel, practical and convenient 'NOSE' approach

An expeditious, simple, highly efficient, practical and green protocol for the N-formylation of alkyl/aryl amines and indole derivatives catalyzed by novel nano rod-shaped basic Al2O3 under solvent-free conditions has been developed. The catalyst is efficiently recycled up to the 5th run, an important point in the domain of green chemistry. The methodology provides cleaner conversion, shorter reaction times and high selectivity which makes the protocol attractive. The Royal Society of Chemistry 2012.

Synthesis and structural analysis of (e)-2-(2'-nitrovinyl)indoles from the corresponding 2-formylindole derivatives

Preparation of 2-formylindoles was carried out from the appropriate methylindole by oxidation with selenium dioxide and by Vilsmeier formylation. The 2-(2'-nitrovinyl)indoles have been obtained by condensation of 2-formylindoles with nitroalkanes in the presence of ammonium chloride in good yields. In this reaction, only the (E)-isomer of the 2-(2'-nitrovinyl)indoles was observed by 1H nmr and NOE experiments. Evidence for an extended conjugation through the double bond and the nitro group can be evaluate by the deshielding effect on the olefinic protons. Moreover, the non-Beer's law behaviour in the uv-visible spectra suggest the existence of some sort of complex for these compounds.

Neat formic acid: An excellent N-formylating agent for carbazoles, 3- alkylindoles, diphenylamine and moderately weak nucleophilic anilines

Neat formic acid alone efficiently N-formylates carbazoles, 3- alkylindoles, diphenylamine and even moderately weak nucleophilic anilines to furnish the corresponding N-formyl derivatives in 72-87% yields.

First electrophilic substitutions of 3-substituted indoles with diethoxycarbenium tetrafluoroborate: Functionalized indole derivatives

The indoles 2a-2c react with diethoxycarbenium tetrafluoroborate (1) to furnish the indolecarbaldehydes 3a-3d. In the thermodynamically controlled reaction of 3-methylindole (2a) with 1 the tris(indolyl)methane 4 and diskatole (5), are formed in addition. The limitations of these reactions are discussed and evidence is presented for a C-3-ipso-attack and a Wagner-Meerwein rearrangement, respectively, leading to the formation of 3b or 3d.

Reactions of Electron-rich Heterocycles with Orthocarboxylic Acid Derivatives, 9. - Acylation of Indole and Methylindoles with Dialkoxycarbenium Tetrafluoroborates

Indole and some methylindoles 1 were acylated regioselectively with dialkoxycarbenium tetrafluoroborates 2 under mild conditions.The formyl cation equivalent 2a' reacts with excess of indoles 1 to give the bisindolylcarbenium tetrafluoroborates 13a-d.

Formylation of Indoles with Formic Acid

Formylation of indoles was carried out in formic acid. 3-Unsubstituted indoles were formylated preferentially at C-3 and 3-substituted indoles were formylated at N-1; C-2 was not formylated in either case.Keywords - formylation; indole; formic acid; formylindole; tryptophan

Pronounced Aldehydic Character of N-Formylindoles: Part II - Preparation, PMR and Mass Spectrometric Study of Their 4-Nitrophenyl- and 2,4-Dinitrophenyl-hydrazones

N-Formylindoles (1A-H) exhibit pronounced aldehydic character as revealed by the formation of 4-nitrophenylhydrazones (2A-E) and 2,4-dinitrophenylhydrazones (2F-J).The N-formylindoles (1E-G) bearing phenyl groups at 2- and 3-positions do not form either 4