335032-69-4

Basic information

• Product Name: 1,5-dimethyl-1H-indole-3-carbaldehyde
• Synonyms: 1,5-dimethyl-1H-indole-3-carbaldehyde;1,5-dimethyl-1H-indole-3-carbaldehyde(SALTDATA: FREE);1H-Indole-3-carboxaldehyde, 1,5-dimethyl-
• CAS NO: 335032-69-4
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.214
• Mol File: 335032-69-4.mol

Chemical Properties

• Boiling Point: 336.4°C at 760 mmHg
• Flash Point: 157.3°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 1,5-dimethyl-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dimethyl-1H-indole-3-carbaldehyde(335032-69-4)
• EPA Substance Registry System: 1,5-dimethyl-1H-indole-3-carbaldehyde(335032-69-4)

Safety Data

• Hazardous Substances Data: 335032-69-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1,5-dimethyl-1H-indole-3-carbaldehyde is used as an intermediate in the production of various pharmaceuticals, contributing to the synthesis of different medicinal compounds.
Used in Fragrance Industry:
It is utilized as a fragrance ingredient in perfumes and personal care products, adding unique scents and enhancing the sensory experience of these products.
Used in Medicinal Chemistry and Drug Discovery:
Due to its distinctive chemical structure, 1,5-dimethyl-1H-indole-3-carbaldehyde may have potential applications in medicinal chemistry and drug discovery, serving as a lead compound for the development of new drugs.
Used in Biological Research:
1,5-dimethyl-1H-indole-3-carbaldehyde has been studied for its potential biological activities, which may lead to its use in the development of novel therapeutic agents or as a tool in biological and medical research.

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

Upstream product

• 27816-53-1 1,5-dimethyl-1H-indole 
• 50-00-0 formaldehyd 
• 298-12-4 Glyoxilic acid 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 67-68-5 dimethyl sulfoxide 

Relevant articles and documents

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.

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.

Visible-Light-Mediated α-Oxygenation of 3-(N,N-Dimethylaminomethyl)-Indoles to Aldehydes

The visible-light-mediated oxygenation of 3-N,N-(dimethylaminomethyl)-indoles bearing various substituents afforded a series of 3-carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)-vincorine is described as well.

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.

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

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.

The ammonium-promoted formylation of indoles by DMSO and H2O

DMSO and H2O is an efficient combination in the NH 4OAc-promoted formylation of indole, where DMSO serves as a C1 carbon source. The mechanism study reveals that the procedure involves a usual and unusual Pummerer reaction.

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

Copper-catalyzed aerobic methyl/methylene oxygenation and C-H formylation with a DABCO-DMSO system for the synthesis of carbonyl indoles and pyrroles

Copper-catalyzed aerobic methyl/methylene oxygenation of substituted indoles and pyrroles was developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additive in dimethyl sulfoxide (DMSO). Similar aerobic catalytic conditions could also be utilized for direct C-H formylation of C(3) on indoles and C(2) on pyrroles.

FAB I INHIBITORS

Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.