54904-22-2

Basic information

• Product Name: 5-CHLOROINDOLE-3-PROPIONIC ACID
• Synonyms: 5-CHLOROINDOLE-3-PROPIONIC ACID;3-(5-chloro-1H-indol-3-yl)propanoic acid
• CAS NO: 54904-22-2
• Molecular Formula: C₁₁H₁₀ClNO₂
• Molecular Weight: 223.66
• Mol File: 54904-22-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 447.9 °C at 760 mmHg
• Flash Point: 224.7 °C
• Appearance: /
• Density: 1.417 g/cm³
• Vapor Pressure: 8.31E-09mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 5-CHLOROINDOLE-3-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROINDOLE-3-PROPIONIC ACID(54904-22-2)
• EPA Substance Registry System: 5-CHLOROINDOLE-3-PROPIONIC ACID(54904-22-2)

Safety Data

• Hazardous Substances Data: 54904-22-2(Hazardous Substances Data)

Usage

General Description

5-Chloroindole-3-propionic acid is a chemical compound that consists of an indole ring with a chlorine atom at the 5 position and a propionic acid side chain attached to the 3 position. 5-CHLOROINDOLE-3-PROPIONIC ACID is often used in organic synthesis and chemical research as a building block for creating more complex molecules. It has potential applications in the pharmaceutical industry as a precursor in the synthesis of pharmaceutical drugs. Additionally, 5-Chloroindole-3-propionic acid has been studied for its potential biological and pharmacological activities, including its effects on the central nervous system. Overall, this compound has diverse potential uses in the fields of chemistry and drug discovery.

InChI:InChI=1/C11H10ClNO2/c12-8-2-3-10-9(5-8)7(6-13-10)1-4-11(14)15/h2-3,5-6,13H,1,4H2,(H,14,15)

Upstream product

• 830-96-6 Indole-3-propionic acid 
• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 1207962-36-4 3-(5-chloro-1H-indol-3-yl)acrylic acid 
• 1421282-90-7 ethyl-3-(5-chloro-1H-indol-3-yl)acrylate 
• 54904-12-0 ethyl 5-chloro-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate 
• 54904-18-6 3-(2-carboxyethyl)-5-chloro-1H-indole-2-carboxylic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 17422-32-1 5-chloro-1H-indole 
• 79-10-7 acrylic acid 
• 221188-29-0 ethyl 3-(5-chloro-1H-indol-3-yl)propanoate 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 170232-13-0 3-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-propionic acid 
• 170232-12-9 3-[5-Chloro-1-(4-fluorophenyl)-3-1H-indolyl]propanol 
• 1026857-54-4 Methanesulfonic acid 3-[5-chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-propyl ester 
• 342636-62-8 Methyl 5-Chloro-1H-indole-3-propionate 

Relevant articles and documents

A Structure-Guided Switch in the Regioselectivity of a Tryptophan Halogenase

Flavin-dependent halogenases are potentially useful biocatalysts for the regioselective halogenation of aromatic compounds. Haloaromatic compounds can be utilised in the synthesis and biosynthesis of pharmaceuticals and other valuable products. Here we report the first X-ray crystal structure of a tryptophan 6-halogenase (SttH), which enabled key residues that contribute to the regioselectivity in tryptophan halogenases to be identified. Structure-guided mutagenesis resulted in a triple mutant (L460F/P461E/P462T) that exhibited a complete switch in regioselectivity; with the substrate 3-indolepropionate 75 % 5-chlorination was observed with the mutant in comparison to 90 % 6-chlorination for the wild-type SttH. This is the first clear example of how regiocomplementary halogenases can be created from a single parent enzyme. The biocatalytic repertoire of SttH was also expanded to include a range of indolic and non-indolic substrates.

Synthesis, characterization, and SAR studies of new (1H-indol-3-yl)alkyl-3- (1H-indol-3-yl)propanamide derivatives as possible antimicrobial and antitubercular agents

In this article, we report herein the SAR studies of a series of (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamide 10(a-j), 11(a-j). The synthesized compounds were evaluated for their preliminary in vitro antibacterial, antifungal activity and were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. The synthesized compounds displayed interesting antimicrobial activity.

2-aryl indole derivatives and their use as therapeutic agents

The present invention relates compounds of the formula (I): wherein R1a, R1b; and R2 represent a variety of substituents; R3 represents an optionally substituted phenyl, biphenyl or naphthyl or heteroaryl group; R4 represents hydrogen, C1-6alkyl, carbonyl (=O), (CH2)pphenyl or a C1-2alkylene bridge across the piperidine ring; R5 and R6 each independently represent a variety of substituents; or R5 and R6 together are linked so as to form an optionally substituted 5-or 6-membered ring; X represents an oxygen or a sulfur atom, two hydrogen atoms, ═NH or ═N(C1-6alkyl); Y is a straight or branched C1-4alkylene, C2-4alkenylene or C2-4alkynylene chain; the dotted line represents an optional double bond; m is zero or an integer from 1 to 4; n is an integer from 1 to 4; and p is an integer from 1 to 4; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migaine, emesis or postherpetic neuralgia.