58176-56-0

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dimethyl-6-methoxyindole is used as a key intermediate in the synthesis of various bioactive compounds, contributing to the development of new drugs. Its aromatic structure and functional groups make it a valuable component in the creation of pharmaceutical agents with diverse therapeutic applications.
Used in Fragrance Industry:
In the fragrance industry, 2,3-Dimethyl-6-methoxyindole is utilized as a raw material for the production of fragrance ingredients. Its sweet, floral-like scent adds depth and complexity to perfumes and other scented products, enhancing their appeal and longevity.
Used in Organic Synthesis:
2,3-Dimethyl-6-methoxyindole serves as a versatile building block in organic synthesis, enabling the creation of a wide range of chemical compounds. Its unique structure and properties make it suitable for various chemical reactions, facilitating the synthesis of complex organic molecules for diverse applications.

InChI:InChI=1/C11H13NO/c1-7-8(2)12-11-6-9(13-3)4-5-10(7)11/h4-6,12H,1-3H3

Upstream product

• 15384-39-1 (3-methoxyphenyl)hydrazine 
• 78-93-3 butanone 
• 380383-81-3 tert-butyl 1-(3-methoxyphenyl)hydrazinecarboxylate 
• 513-86-0 3-hydroxy-2-butanon 
• 536-90-3 m-Anisidine 
• 513-85-9 2.3-butanediol 

Downstream Products

• 68289-71-4 2,3-dimethyl-6-methoxy-7-nitroindole 
• 68289-70-3 6-methoxy-2,3-dimethyl-5-nitroindole 

Relevant academic research and scientific papers

Improved indole syntheses from anilines and vicinal diols by cooperative catalysis of ruthenium complex and acid

By developing a new and efficient dinuclear catalyst [Ru(CO) 2(Xantphos)]2 [Xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethyl-9H-xanthene], an improved synthesis of indole from vicinal diols and anilines by cooperative catalysis of ruthenium complex and p-TSA (para-toluenesufonic acid) has been demonstrated. The presented synthetic protocol allows assembling a wide range of products in an efficient manner. Comparing to the existed protocols, our indole syntheses can be achieved at lower reaction temperature, in shorter reaction time, and with improved substrate tolerance.

Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols

A straightforward and atom-economical method is described for the synthesis of 2,3-disubstituted indoles. Anilines and 1,2-diols are condensed under neat conditions with catalytic amounts of either [Cp*IrCl2] 2/MsOH or RuCl3·xH2O/phosphine (phosphine = PPh3 or xantphos). The reaction does not require any stoichiometric additives and only produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy, chloro and fluoro substituents can participate in the cyclocondensation. Meta-substituted anilines give good regioselectivity for 6-substituted indoles, while unsymmetrical diols afford excellent regioselectivity for the indole isomer with an aryl or large alkyl group in the 2-position. The mechanism for the cyclocondensation presumably involves initial formation of the α-hydroxyketone from the diol. The ketone subsequently reacts with aniline to generate the α-hydroxyimine which rearranges to the corresponding α-aminoketone. Acid- or metal-catalysed electrophilic ring-closure with the release of water then furnishes the indole product.

Synthesis and rearrangements of 7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]-and 7h-pyrrolo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines

7H-Pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines were synthesized by the reactions of 2-ethoxymethyleneamino-1H-pyrrole-3-carbonitriles with acid hydrazides and by the reactions of aminoiminopyrimidines (prepared based on the above-mentioned carbonitriles) with acid chlorides.

Expedient synthesis of indoles from N-Boc arylhydrazines

The readily available N-Boc arylhydrazines undergo efficient Fischer cyclizations to provide the indoles in good yields, when reacted with enolizable ketones.