38292-40-9

Usage

Uses

Used in Perfumery:
1,2-Dimethyl-1H-indole-3-carboxaldehyde is used as a fragrance ingredient for its strong, sweet, and floral odor, which is key in enhancing the scent profiles of many perfumes.
Used in Pharmaceutical Industry:
1,2-Dimethyl-1H-indole-3-carboxaldehyde is utilized as a pharmaceutical intermediate due to its potential medicinal properties, including anti-inflammatory and anti-cancer effects, making it a valuable component in the development of new drugs.
Used in Dye Production:
In the dye industry, 1,2-Dimethyl-1H-indole-3-carboxaldehyde is employed as a chemical intermediate, contributing to the synthesis of various dyes that require its unique chemical structure.
Used in Consumer Products:
1,2-Dimethyl-1H-indole-3-carboxaldehyde is an important ingredient in a wide range of consumer products, particularly in the fragrance and flavor sectors, where its distinctive scent adds value to the final product.

InChI:InChI=1/C11H11NO/c1-8-10(7-13)9-5-3-4-6-11(9)12(8)2/h3-7H,1-2H3

Upstream product

• 875-79-6 1,2-dimethylindole 
• 93-61-8 N-methyl-N-phenylformamide 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 19012-03-4 N-methyl-3-formylindole 
• 65037-61-8 1,2-Dimethyl-3-vinylindole 
• 128746-62-3 2,3-dibromo-1-methyl-1H-indole 
• 67-68-5 dimethyl sulfoxide 
• 1971-46-6 1,2,3-trimethylindole 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 75-50-3 trimethylamine 

Downstream Products

• 124210-01-1 2-Benzhydrylidene-3-[1-(1,2-dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-succinic acid 4-ethyl ester 
• 124210-02-2 2-Cyclohexylidene-3-[1-(1,2-dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-succinic acid 4-ethyl ester 
• 134828-30-1 2-(1,2-Dimethyl-1H-indol-3-yl)-5,7-dimethyl-1,3-diaza-tricyclo[3.3.1.1^3,7]decan-6-one 
• 51072-84-5 1,2-dimethyl-1H-indole-3-carbonitrile 
• 1226783-81-8 C₂₁H₂₁NO₂ 
• 338997-02-7 1,2-dimethyl-1H-indole-3-carbaldehyde oxime 
• 1333430-05-9 C₂₁H₂₂N₂O₃ 
• 1333429-65-4 (E)-3-(1,2-dimethyl-1H-indol-3-yl)acrylaldehyde 
• 1333429-80-3 2-((2S,3S,4S)-9-methyl-3-nitro-2-phenyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)acetaldehyde 
• 124210-06-6 2-Benzhydrylidene-3-[1-(1,2-dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-succinic acid 
• 124210-11-3 E-(1,2-Dimethyl-3-indolylmethylene)diphenylmethylenesuccinic Anhydride 
• 124210-07-7 E-(1,2-Dimethyl-3-indolylmethylene)cyclohexylidenesuccinic Acid 
• 124210-12-4 E-(1,2-Dimethyl-3-indolylmethylene)cyclohexylidenesuccinic Anhydride 
• 210626-91-8 (E)-3-{2-[2-(2-Iodo-phenyl)-ethyl]-1-methyl-1H-indol-3-yl}-2-methyl-acrylic acid ethyl ester 

Relevant academic research and scientific papers

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals

An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade, respectively, leading to chiral polycyclic tetrahydrocarbazole and chromane derivatives with excellent diastereo- and enantioselectivities.

Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.

Screening metal-free photocatalysts from isomorphic covalent organic frameworks for the C-3 functionalization of indoles

The visible-light-driven organic transformation using two-dimensional covalent organic frameworks (2D-COFs) as metal-free heterogeneous photocatalysts is a green and sustainable approach, and it has gained a surge of interest by virtue of the photosensitizer's high crystallinity, abundant porosity, outstanding stability, excellent light-harvesting ability and tunable structure. However, the guiding principle for designing, constructing and selecting COF-based photocatalysts has not been put forward so far. Herein, we contribute a fascinating strategy to guide the acquisition of excellent framework photocatalysts, which is to screen them from a series of isomorphic COFs. As a proof of concept, three new isomorphic pyrene-based 2D-COFs (COF-JLU23, COF-JLU24 and COF-JLU25) with variable linkers were successfully synthesized. In addition to having similar crystallinity and porosity with the same pore size and shape, their absorption, emission, bandgap, energy level, transient photocurrent response and photocatalytic activity could be easily adjustedviaconfiguring different linkers in frameworks. Indeed, COF-JLU24 with electron donor-acceptor characteristics exhibited the best photocatalytic activity among the three isomorphic COFs for C-3 functionalization reactions of indoles, even better than that of the metal-free photocatalyst g-C3N4. More importantly, the screened COF-JLU24 as a metal-free photocatalyst still displayed extensive substrate adaptability and excellent recyclability. We anticipate that this strategy will become a robust rule of thumb for fast access to COF-based photocatalysts. In addition, we still highlight that the present study broadens the applied frontier of COF-based photocatalysts.

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3

A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

Phenylpiperazine type UBE2F small molecule inhibitor and synthesis method thereof

The invention discloses a phenylpiperazine type UBE2F small molecule inhibitor and a synthesis method thereof, discloses a phenylpiperazine type compound represented by the general formula I or a pharmaceutically acceptable salt thereof, and further discloses a synthesis route of the general formula I and a synthesis method of each step. As a small molecule inhibitor target at UBE2F, that phenylpiperazine type compound of the present invention effectively suppresses the growth of tumor cell by preventing the G2/M process of cell cycle and inducing apoptosis of human tumor cells. Therefore, thecompound is a new class of specific anti-tumor drugs by targeting UBE2F.

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst

A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.

Method for performing formylation reaction of indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs)

The invention discloses a method for performing formylation reaction of an indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs). The method is characterized in thatin an oxygen-containing atmosphere and water/organic mixed solvent system, the indole compound and a methylamine compound are subjected to formylation reaction under the catalytic action of iodized salt and CMPs and illumination conditions so as to obtain a 3-formaldehyde indole compound. The method has mild reaction conditions, can be implemented under room temperature and illumination conditionsand can be used for obtaining the target product in high selectivity and high yield, the reaction belongs to heterogeneous catalysis reaction, the catalyst can be recovered and recycled, and industrial production is facilitated.

Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers

Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.

Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles

An unprecedented technique for the in situ generation of indolyl ortho-quinodimethanes from 2-methylindole-based methylenemalononitriles by amine-mediated remote C(sp3)?H deprotonation was developed. These intermediates were efficiently trapped by diverse enals to provide a rapid entry to 2,9-dihydro-1H-carbazole-3-carboxyaldehyde structures through a formal asymmetric [4+2] eliminative cycloaddition governed by a α,α-diphenylprolinol trimethylsilyl ether catalyst.