16886-10-5

Basic information

• Product Name: 3-BENZYLINDOLE
• Synonyms: 3-BENZYLINDOLE;3-Benzyl-1H-indole;Nsc26860;3-Benzylindol
• CAS NO: 16886-10-5
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.27
• Mol File: 16886-10-5.mol
• Article Data: 63

Chemical Properties

• Boiling Point: 382.2°Cat760mmHg
• Flash Point: 168.9°C
• Appearance: /
• Density: 1.143g/cm³
• Vapor Pressure: 1.05E-05mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 3-BENZYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZYLINDOLE(16886-10-5)
• EPA Substance Registry System: 3-BENZYLINDOLE(16886-10-5)

Safety Data

• Hazardous Substances Data: 16886-10-5(Hazardous Substances Data)

Usage

General Description

3-Benzylindole, also known as 1H-indole-3-ethanamine, is a chemical compound with the molecular formula C16H17N. It is a substituted indole derivative, with a benzyl group attached to the third carbon of the indole ring. 3-Benzylindole is primarily used in the research and pharmaceutical industries for its potential therapeutic properties, including its role as a serotonin receptor agonist and potential antipsychotic effects. It is also known to have potential anti-inflammatory and anticancer properties, making it a subject of interest for further study and development. Additionally, 3-Benzylindole has been studied for its potential use as a fluorescent and chromophore for various applications in chemical and biological research.

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 
• 1004541-89-2 (+/-)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-benzyl-1H-indole 
• 1360772-06-0 (R)-3-benzylindoline 
• 1393444-72-8 3-((4-tert-butylphenyl)(phenyl)methyl)-1H-indole 
• 1428236-59-2 C₂₆H₂₃NO₃ 
• 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 articles and documents

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.

-

-

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.

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.