38693-08-2

Basic information

• Product Name: 2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE
• Synonyms: 2-chloro-1-(2-methyl-1H-indol-3-yl)ethan-1-one
• CAS NO: 38693-08-2
• Molecular Formula: C₁₁H₁₀ClNO
• Molecular Weight: 207.66
• Mol File: 38693-08-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.7 °C
• Appearance: /
• Density: 1.289 g/cm³
• Vapor Pressure: 4.38E-06mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE(38693-08-2)
• EPA Substance Registry System: 2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE(38693-08-2)

Safety Data

• Hazardous Substances Data: 38693-08-2(Hazardous Substances Data)

Usage

General Description

2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE, also known as 2-chloro-1-(2-methylindol-3-yl)ethanone, is an organic compound with the molecular formula C11H10ClNO. It is a chlorinated ketone that contains a methyl-substituted indole group. 2-CHLORO-1-(2-METHYL-1H-INDOL-3-YL)-ETHANONE is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is known for its use in the production of various indole derivatives, which are important in the pharmaceutical industry for their potential as anticancer, antiviral, and antibacterial agents. The compound has also been studied for its potential use in the treatment of neurological disorders and as a building block for the synthesis of various organic molecules.

InChI:InChI=1/C11H10ClNO/c1-7-11(10(14)6-12)8-4-2-3-5-9(8)13-7/h2-5,13H,6H2,1H3

Upstream product

• 79-04-9 chloroacetyl chloride 
• 95-20-5 2-methyl-1H-indole 

Downstream Products

• 76397-72-3 3-(2-methyl-1H-indol-3-yl)-3-oxopropanenitrile 
• 337470-17-4 2-dimethylamino-1-(2-methyl-indol-3-yl)-ethanone 
• 27463-04-3 2-Methyl-3-hydroxyacetyl-indol 
• 2731-06-8 2-methyltryptamine 
• 2826-95-1 2-methyltryptamine hydrochloride 
• 264877-15-8 dithiocarbonic acid S-[1-cyanomethyl-4-(2-methyl-1H-indol-3-yl)-4-oxo-butyl] ester O-ethyl ester 
• 113369-34-9 acid oxalate of N-<2-(2-methyl-3-indolyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine 
• 113369-31-6 1-(2-methyl-3-indolyl)-2-<2-(3,4-dimethoxyphenyl)ethyl>aminoethanol 
• 89-52-1 o-acetylamino-benzoic acid 
• 113369-29-2 1-(2-methyl-3-indolyl)-2-<2-(3,4-dimethoxyphenyl)ethyl>aminoethanone hydrochloride 
• 50825-19-9 4-(2-methyl-1H-indol-3-yl)thiazol-2-amine 

Relevant articles and documents

4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines as novel antimicrobial agents: Synthesis, in silico and in vitro evaluation

This manuscript deals with the synthesis and computational and experimental evaluation of the antimicrobial activity of twenty-nine 4-(indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (?) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive. Compound 5x was the most promising, with an MIC in the range of 0.06–0.12 mg/mL, followed by 5d and 5m. An evaluation of these three compounds against resistant strains, namely MRSA P. aeruginosa and E. coli, revealed that they were more potent against MRSA than ampicillin. Furthermore, compounds 5m and 5x were superior inhibitors of biofilm formation, compared to ampicillin and streptomycin, in terms Compounds 5d, 5m, and 5x interact with streptomycin in additive manner. The antifungal activity of some compounds exceeded or was equipotent to those of the reference antifungal agents bifonazole and ketoconazole. The most potent antifungal agent was found to be compound 5g. Drug likeness scores of compounds was in a range of ?0.63 to 0.29, which is moderate to good. According to docking studies, E. coli MurB inhibition is probably responsible for the antibacterial activity of compounds, whereas CYP51 inhibition was implicated in antifungal activity. Compounds appeared to be non-toxic, according to the cytotoxicity assessment in MRC-5 cells.

Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate

A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.

An expedient construction of seven-membered rings adjoining aromatic systems

An unusual radical-mediated fusion of a seven-membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonares (xanthates). This type of annelation (an example is shown), which was hitherto very diff