1463-60-1

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxaldehyde, 5-methyl(9CI) is used as a key intermediate in the synthesis of pharmaceuticals for its ability to form complex molecular structures that can exhibit therapeutic effects. Its unique chemical properties allow it to be incorporated into a variety of drug molecules, contributing to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical sector, 1H-Indole-2-carboxaldehyde, 5-methyl(9CI) serves as a building block in the creation of compounds that can be used in pest control and crop protection. Its reactivity and stability make it suitable for the development of effective and targeted agrochemicals.
Used in Fragrance Industry:
1H-Indole-2-carboxaldehyde, 5-methyl(9CI) is used as a component in the formulation of fragrances due to its strong and distinctive odor. It can be found in various perfumes and scented products, adding depth and complexity to the overall scent profile.
Used as a Reagent in Organic Chemistry:
1H-Indole-2-carboxaldehyde, 5-methyl(9CI) also functions as a reagent in organic chemistry reactions, facilitating the synthesis of a range of organic compounds. Its versatility in reactions makes it a valuable tool for researchers and chemists in various scientific applications.

Upstream product

• 16382-15-3 5-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 10241-97-1 5-methylindole-2-carboxylic acid 
• 55795-87-4 (5-methyl-1H-indol-2-yl)methanol 
• 102870-03-1 5-methylindole-2-carboxylic acid methyl ester 
• 16732-81-3 6-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 56813-19-5 6-methylindol-2-ylmethanol 

Downstream Products

• 1587723-12-3 7-methyl-1-phenyl-1H,4H-pyrazolo[4,3-b]indole 

Relevant academic research and scientific papers

Addition of a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp2 Carbon for Protonation and Formal [4+2] Reaction

The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.

One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives

A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.

Highly enantioselective synthesis of functionalized azepino[1,2-a] indoles via NHC-catalyzed [3+4] annulation

The enantioselective [3+4] annulation of 3-formylindol-2-methyl-malonates with 2-bromoenals catalyzed by NHCs is described to afford functionalized azepino[1,2-a]indoles in high yields with excellent enantioselectivities. This method, in which the 3-formyl group in indoles acts as a necessary mediating group, provided cycloaddition products under mild conditions.

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization: Sustainable access to indole-2,3-fused diazocanes

An unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o-aminoanilines was developed to assemble polycyclic indole-2,3-fused diazocanes in one step. This novel methodol