883-55-6

Basic information

• Product Name: (5-chloro-1H-indol-3-yl)(oxo)acetyl chloride
• CAS NO: 883-55-6
• Molecular Formula: C₁₀H₅Cl₂NO₂
• Molecular Weight: 242.0582
• Mol File: 883-55-6.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 444.437°C at 760 mmHg
• Flash Point: 222.588°C
• Density: 1.573g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: (5-chloro-1H-indol-3-yl)(oxo)acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (5-chloro-1H-indol-3-yl)(oxo)acetyl chloride(883-55-6)
• EPA Substance Registry System: (5-chloro-1H-indol-3-yl)(oxo)acetyl chloride(883-55-6)

Safety Data

• Hazardous Substances Data: 883-55-6(Hazardous Substances Data)

Usage

Description

(5-chloro-1H-indol-3-yl)(oxo)acetyl chloride is a chlorinated acetyl chloride derivative of 5-chloroindole, a heterocyclic organic compound. It is characterized by its reactive acetyl group and a chlorine atom, which makes it a versatile building block for the synthesis of various organic compounds through acylation reactions. Its structural properties and reactivity contribute to its utility in the production of pharmaceuticals, agrochemicals, and other fine chemicals. However, due to its potential reactivity and toxicity, it should be handled with caution.

Uses

Used in Pharmaceutical Synthesis:
(5-chloro-1H-indol-3-yl)(oxo)acetyl chloride is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its reactivity allows for the creation of new molecules with potential therapeutic applications, contributing to the development of novel drugs.
Used in Agrochemical Production:
In the agrochemical industry, (5-chloro-1H-indol-3-yl)(oxo)acetyl chloride is used as a building block for the development of new agrochemicals. Its incorporation into these compounds can lead to enhanced pest control and crop protection, ultimately benefiting agricultural productivity.
Used in Organic Synthesis for Fine Chemicals:
(5-chloro-1H-indol-3-yl)(oxo)acetyl chloride is also utilized in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, dyes, and specialty chemicals. Its unique properties enable the production of a wide range of valuable compounds with specific applications.

Upstream product

• 79-37-8 oxalyl dichloride 
• 17422-32-1 5-chloro-1H-indole 

Downstream Products

• 97529-48-1 2-[2-(5-Chloro-1H-indol-3-yl)-2-oxo-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 140677-09-4 2-(5-Chloro-1H-indol-3-yl)-2-oxo-N-phenethyl-acetamide 
• 107610-02-6 2-(5-Chloro-1H-indol-3-yl)-N-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-acetamide 
• 119284-51-4 N-(5-chloroindol-3-ylglyoxylyl)dopamine 
• 140677-21-0 2-(5-Chloro-1H-indol-3-yl)-N-[2-(4-chloro-phenyl)-ethyl]-2-oxo-acetamide 
• 170232-31-2 N-benzyl-N-methyl-2-(5-chloro-1H-indol-3-yl)-2-oxoacetamide 
• 1329121-25-6 (Z)-5-(2-(5-chloro-1H-indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one 
• 914658-49-4 6-chloro-4-oxo-N'-phenyl-1,4-dihydroquinoline-3-carboxamide 

Relevant articles and documents

Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines

A series of substituted di-indolglyoxylamido-spermine analogues were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-positive bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the 5-bromo- and 6-chloro-indole analogues which also exhibited modest activity (MIC 34–50 μM) towards the Gram-negative bacteria Escherichia coli and Klebsiella pneumoniae. Several analogues enhanced the activity of doxycycline towards the Gram-negative bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogues (5-Br, 7-F, 5-Me, 7-Me, 7-OMe) which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the 5-Br and 7-F analogues were attributed to the ability to disrupt the integrity of, and depolarize, bacterial membranes.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

Indole compound with antivirus activity in radix isatidis and derivative of indole compound

The invention discloses an indole compound extracted from radix isatidis shown in a general formula (I) and a derivative of the indole compound, as well as a salt acceptable on pharmacy, a preparation method of the compound, and a medicinal composite. The compound has apparent HIV-resisting activity and influenza virus-resisting activity, and can be used for preparing drugs or healthcare products for resisting HIV or influenza viruses. (The formula is shown in the description.).