161261-55-8

Basic information

• Product Name: 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde
• Synonyms: 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde;1H-indole-3-carboxaldehyde, 1-(2-hydroxyethyl)-;1-(2-hydroxyethyl)-3-indolecarboxaldehyde;1-(2-hydroxyethyl)indole-3-carbaldehyde
• CAS NO: 161261-55-8
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.22
• Mol File: 161261-55-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde(161261-55-8)
• EPA Substance Registry System: 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde(161261-55-8)

Safety Data

• Hazardous Substances Data: 161261-55-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde is used as an intermediate for the synthesis of various bioactive compounds. Its unique structure allows for the creation of a wide range of pharmaceutical products, contributing to the development of new treatments and therapies.
Used in Chemical Industry:
In the chemical industry, 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde serves as a key component in the production of different organic molecules. Its functional groups facilitate various chemical reactions, enabling the synthesis of complex compounds for a multitude of applications.
Used in Research Laboratories:
1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde is also utilized as a reagent in organic synthesis within research laboratories. Its presence aids in the development of new chemical processes and the exploration of novel synthetic pathways, further expanding the potential applications of 1-(2-hydroxyethyl)-1H-indole-3-carbaldehyde in various scientific fields.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 540-51-2 2-bromoethanol 
• 121459-15-2 2-(1H-indol-1-yl)ethanol 
• 24297-59-4 1-indolylacetic acid 
• 125315-16-4 2-(1H-indol-1-yl)ethyl acetate 
• 120-72-9 indole 
• 50-00-0 formaldehyd 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 

Relevant articles and documents

N-(Hydroxyalkyl) derivatives of tris(1H-indol-3-yl)methylium salts as promising antibacterial agents: Synthesis and biological evaluation

The wide spread of pathogens resistance requires the development of new antimicrobial agents capable of overcoming drug resistance. The main objective of the study is to elucidate the effect of substitutions in tris(1H-indol-3-yl)methylium derivatives on their antibacterial activity and toxicity to human cells. A series of new compounds were synthesized and tested. Their antibacterial activity in vitro was performed on 12 bacterial strains, including drug resistant strains, that were clinical isolates or collection strains. The cytotoxic effect of the compounds was determined using an test with HPF-hTERT (human postnatal fibroblasts, immortalized with hTERT) cells. The activity of the obtained compounds depended on the carbon chain length. Derivatives with C5–C6 chains were more active. The minimum inhibitory concentration (MIC) of the most active compound on Gram-positive bacteria, including MRSA, was 0.5 μg/mL. Compounds with C5–C6 chains also revealed high activity against Staphylococcus epidermidis (1.0 and 0.5 μg/mL, respectively) and moderate activity against Gram-negative bacteria Escherichia coli (8 μg/mL) and Klebsiella pneumonia (2 and 8 μg/mL, respectively). However, they have no activity against Salmonella cholerasuis and Pseudomonas aeruginosa. The most active compounds revealed higher antibacterial activity on MRSA than the reference drug levofloxacin, and their ratio between antibacterial and cytotoxic activity exceeded 10 times. The data obtained provide a basis for further study of this promising group of substances.

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.

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.

Synthesis of 1-Substituted Indole-3-carboxaldehydes Related to Acyclic Nucleosides and Their Condensed Pyrenyl Derivatives

Indole-3-carboxaldehyde was N-alkylated to give the corresponding acyclic nucleosides 3a-h which were condensed with 1-pyrenamine and 1-acetylpyrene to give 5a,c,e-g and 7b-d,e,g, respectively. The Schiff's bases 5a and 5e with 2-hydroxyethyl and methylthiomethyl N-1-substituents were found moderate active against HIV-1.