19293-60-8

Usage

Uses

Used in Pharmaceutical Industry:
(1-Methyl-1H-indol-3-yl)-methylamine is used as a synthetic intermediate for the development of new syntheses of indole phytoalexins and related compounds. Phytoalexins are antimicrobial secondary metabolites produced by plants in response to pathogen attack, and they have potential applications in the pharmaceutical industry for their bioactive properties.
Used in Chemical Research:
(1-Methyl-1H-indol-3-yl)-methylamine can also be utilized in chemical research as a building block for the synthesis of more complex organic molecules, particularly those with potential applications in the fields of medicinal chemistry and drug discovery.
Used in Material Science:
(1-Methyl-1H-indol-3-yl)-methylamine may find applications in material science, particularly in the development of novel materials with specific properties, such as light-emitting diodes (LED) or organic photovoltaics, due to the electronic properties of the indole moiety.

InChI:InChI=1/C10H12N2/c1-12-7-8(6-11)9-4-2-3-5-10(9)12/h2-5,7H,6,11H2,1H3

Upstream product

• 24662-37-1 1-methyl-1H-indole-3-carbonitrile 
• 24666-30-6 1-methyl-1H-indole-3-carbaldehyde oxime 
• 19012-03-4 N-methyl-3-formylindole 
• 487-89-8 Indole-3-carboxaldehyde 

Downstream Products

• 440098-91-9 2-[1-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-N-(1-methyl-1H-indol-3-ylmethyl)-2-phenyl-acetamide 
• 19012-03-4 N-methyl-3-formylindole 

Relevant academic research and scientific papers

A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution

A simple and concise approach for the synthesis of cyclobrassinin has been developed through a thiyl radical-mediated intramolecular aromatic substitution, with benzoyl peroxide as an efficient initiator and oxidant. The current method can also be utilized in the synthesis of 6 and 7-membered ring cyclobrassinin analogues in moderate to good yields. The transformation involves a formal radical 6 and 7-endo-trig cyclization of the corresponding dithiocarbamate derivatives, which were generated from indole-3-methanamines and tryptophan.

A novel palladium-catalyzed cyclization of indole phytoalexin brassinin and its 1-substituted derivatives

A novel simple synthetic approach to spiroindoline phytoalexins and their derivatives has been developed. The spirocyclization of brassinin and its 1-substituted derivatives was achieved using palladium catalyst PdCl 2(CH3CN)2 in DMSO at 80°C in the presence of water, methanol or aniline.

New syntheses of indole phytoalexins and related compounds

Synthesis of indole phytoalexins brassinin, brassitin, cyclobrassinin and related compounds via 3-aminomethylindole and its 1-substituted derivatives obtained by nickel boride catalyzed reduction of corresponding aldoximes with sodium borohydride and via [1-(t-butoxycarbonyl)-indol-3-yl]methyl isothiocyanate, the first stable derivative of indol-3-ylmethyl isothiocyanate is described. Antifungal activity of the prepared compounds was examined by using the fungus Bipolaris leersiae by t.l.c. bioassay and quantitative screening was carried out with the selected compounds.