16886-10-5

Usage

Uses

Used in Pharmaceutical Research:
3-Benzylindole is used as a research compound for its potential therapeutic applications, primarily due to its role as a serotonin receptor agonist. This makes it a candidate for the development of treatments targeting various psychiatric and neurological disorders.
Used in Antipsychotic Drug Development:
Given its potential antipsychotic effects, 3-Benzylindole is utilized in the research and development of novel antipsychotic medications, aiming to provide more effective and safer treatment options for patients with psychotic disorders.
Used in Anti-Inflammatory and Anticancer Research:
3-Benzylindole is employed as a subject of study in anti-inflammatory and anticancer research, due to its potential to modulate immune responses and exhibit anticancer activity, which could lead to the discovery of new therapeutic agents for inflammatory and cancerous conditions.
Used in Chemical and Biological Research as a Fluorescent and Chromophore:
3-Benzylindole is used as a fluorescent and chromophore in various applications within chemical and biological research. Its properties allow for its use in imaging studies, detection methods, and as a tool in the development of new analytical techniques.

InChI:InChI=1/C15H13N/c1-2-6-12(7-3-1)10-13-11-16-15-9-5-4-8-14(13)15/h1-9,11,16H,10H2

Upstream product

• 120-72-9 indole 
• 2785-29-7 benzyl potassium 
• 108-88-3 toluene 
• 7511-08-2 3-benzyl-2-oxindole 
• 5457-31-8 (3-indolylmethyl)trimethylammonium iodide 
• 100-44-7 benzyl chloride 
• 74873-29-3 3-Benzyl-2-chloro-1H-indole 
• 81581-98-8 1-[3-Acetyl-2-(1H-indol-3-yl)-2-phenyl-imidazolidin-1-yl]-ethanone 
• 1477-50-5 Indole-2-carboxylic acid 
• 247222-84-0 2-(2-phenylethynyl)phenyl isocyanide 
• 316795-02-5 1-trifluoroacetyl-2-trimethylsilyl-3-benzylindole 
• 23061-14-5 3-benzyl-2-ethylsulfanyl-indole 
• 100-39-0 benzyl bromide 
• 497949-70-9 benzyl N-phenyl-sulfamoylcarbamate 

Downstream Products

• 102015-90-7 3-benzyl-1-dimethylaminomethyl-indole 
• 103271-32-5 bis-(3-benzyl-indol-1-yl)-methane 
• 3377-72-8 2-benzylindole 
• 133477-53-9 1-[5-(3-Benzyl-1H-indol-2-yl)-2-phenyl-pyrazolidin-1-yl]-ethanone 
• 118535-37-8 4-(3-Benzyl-indol-1-yl)-butan-2-one 
• 118535-38-9 4-[2-Benzyl-3-(3-oxo-butyl)-indol-1-yl]-butan-2-one 
• 1360772-06-0 (R)-3-benzylindoline 
• 1393444-72-8 3-((4-tert-butylphenyl)(phenyl)methyl)-1H-indole 
• 1449683-66-2 methyl 2-(3-benzyl-1H-indol-2-yl)acetate 
• 1449683-80-0 (R)-methyl 4a-benzyl-4a,9-dihydro-4H-carbazole-1-carboxylate 

Relevant academic research and scientific papers

Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts

(Chemical Equation Presented) Gramine-Mel salts were useful starting materials for the synthesis of 3-benzyl- and 3-allylindoles by the 1,4-addition of boronic acids to the C=C-C=N linkages generated in situ under Rh(I)-catalysis. On the other hand, under Ir(I) catalysis, the reaction of gramines with indoles was used to produce nonsymmetrical diindolylmethanes.

Regioselective synthesis of 3-alkylindoles mediated by zinc triflate

Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Huenig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a SN1-like pathway, and is general for allylic, benzylic, and tertiary halides.

Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles

Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.

Cobalt-Catalyzed Hydrogenative Transformation of Nitriles

Here, we report the transformation of nitrile compounds in a hydrogen atmosphere. Catalyzed by a cobalt/tetraphosphine complex, hydrogenative coupling of unprotected indoles with nitriles proceeds smoothly in a basic medium, yielding C3 alkylated indoles. In addition, the direct hydrogenation of nitriles under the same conditions yielded primary amines. Isotope labeling experiments, along with a series of control experiments, revealed a reaction pathway that involves nucleophilic addition of indoles and 1,4-reduction of a conjugate imine intermediate. Different from reductive alkylation of indoles under an acidic condition, E1cB elimination is believed to occur in this base-promoted hydrogenative coupling reaction.

Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

Efficient copper-catalyzed synthesis of C3-alkylated indoles from indoles and alcohols

A highly efficient copper(II) catalyst system for alkylation of indoles with alcohols via hydrogen borrowing method has been developed to afford C3-alkylated indoles in good to excellent yields. Cu(OAc)2 in the combination with dppm ligand has been found to be the most suitable catalyst system for this alkylation reaction.

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method

An inexpensive, air-stable, isolable nickel catalyst is reported that can perform chemoselective C3-alkylation of indoles with a variety of alcohols following "borrowing hydrogen". A one-pot, cascade C3-alkylation starting from 2-aminophenyl ethyl alcohols, and thus obviating the need for pre-synthesized indoles, further adds to the broad scope of this method. The reaction is radical-mediated, and is significantly different from other examples, often dictated by metal-ligand bifunctionality. This journal is

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air-and moisture-stable manganese catalyst provides access to either C3-or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.