202584-14-3

Basic information

• Product Name: 1,6-dimethyl-1H-indole-3-carbaldehyde
• Synonyms: 1,6-dimethyl-1H-indole-3-carbaldehyde;1H-Indole-3-carboxaldehyde, 1,6-dimethyl-
• CAS NO: 202584-14-3
• Molecular Formula: C11H11NO
• Molecular Weight: 173.21114
• Mol File: 202584-14-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 1,6-dimethyl-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-dimethyl-1H-indole-3-carbaldehyde(202584-14-3)
• EPA Substance Registry System: 1,6-dimethyl-1H-indole-3-carbaldehyde(202584-14-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 202584-14-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,6-dimethyl-1H-indole-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1,6-dimethyl-1H-indole-3-carbaldehyde is utilized as a precursor in the production of agrochemicals, aiding in the creation of substances that can enhance crop protection and yield.
Used in Organic Synthesis:
1,6-dimethyl-1H-indole-3-carbaldehyde is employed as a reagent in organic synthesis, facilitating the preparation of a wide range of chemical compounds for various applications across different industries.
Used in Research Laboratories:
1,6-dimethyl-1H-indole-3-carbaldehyde is also used in research settings as a reagent for the preparation and study of other chemical compounds, contributing to the advancement of scientific knowledge and the development of new chemical processes.

Upstream product

• 4771-49-7 6-methyl-1H-indole-3-carboxaldehyde 
• 5621-15-8 1,6-dimethyl-1H-indole 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 74-88-4 methyl iodide 
• 3420-02-8 6-methylindole 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 75-50-3 trimethylamine 

Relevant articles and documents

Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.

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.

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

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.

Indole-substituted hydrazide derivatives and uses thereof

The invention discloses indole-substituted hydrazide derivatives and a use thereof, concretely relates to novel indole-substituted hydrazide derivatives and a medicinal composition including the abovecompounds, a use of the derivatives and the medicinal composition in the protection of nerve cells, and also relates to a method for preparing the compounds and the medicinal composition, and a use of the compounds and the medicinal composition in the preparation of drugs for treating diseases associated with glutamate excitotoxicity and oxidative stress damage or free radicals, or neurodegenerative diseases, especially the Alzheimer disease.

CuCl2/TBHP-mediated direct chlorooxidation of indoles

CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.

Facile Synthesis of Carbazoles via a Tandem Iodocyclization with 1,2-Alkyl Migration and Aromatization

A strategy for the synthesis of iodocarbazoles through a tandem iodocyclization with migration and aromatization is presented. This sequential cascade process is concisely conducted at room temperature and in a short time. Moreover, the obtained halides c

Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.

I2-mediated C3-formylation of indoles by tertiary amine and H2O

An I2-promoted 3-formylation of free (N-H) and N-substituted indoles with tetramethylethylenediamine (TMEDA) and H2O as the carbonyl source is achieved, providing 3-formylindole in moderate to excellent yields with good functional gr

The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen

A copper-catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The C-H bonds of indoles were C-3-formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3-formylindoles. Copyright