17630-75-0

Basic information

• Product Name: 5-Chlorooxindole
• Synonyms: 4-chloroindole-2(3h)-one;3-dihydroindole-2-one;5-Chlorooxindole ,99%;5-CHLOROOXINDOLE, 97+%;5-Chloro-1H-indol-2(3H)-one;5-Chorooxindole;5-Chloro-2-oxindole,5-Chlorooxindole;1H-indol-5-yl hypochlorite
• CAS NO: 17630-75-0
• Molecular Formula: C₈H₆ClNO
• Molecular Weight: 167.59
• EINECS: 412-200-9
• Product Categories: oxindoles;blocks;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Indole;Indoles;Heterocycles
• Mol File: 17630-75-0.mol
• Article Data: 47

Chemical Properties

• Melting Point: 194-197 °C(lit.)
• Boiling Point: 348.3 °C at 760 mmHg
• Flash Point: 164.5 °C
• Appearance: Tan powder
• Density: 1.362 g/cm³
• Vapor Pressure: 0.00881mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep Cold
• Solubility: Slightly Soluble (2.0 g/L) (25°C).
• PKA: 13.14±0.20(Predicted)
• CAS DataBase Reference: 5-Chlorooxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chlorooxindole(17630-75-0)
• EPA Substance Registry System: 5-Chlorooxindole(17630-75-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43-52/53-62-36/37/38
• Safety Statements: 22-36/37-61-45-36/37/39-24-37/39-26
• WGK Germany: 2
• Hazardous Substances Data: 17630-75-0(Hazardous Substances Data)

Usage

Description

5-Chloro-2-oxindole (5-Chlorooxindole) is a chemical compound with the molecular formula C8H6ClNO and is characterized by its tan powder appearance. It serves as a starting material for the synthesis of various pharmaceutical compounds and has potential applications in the development of novel drugs.

Uses

Used in Pharmaceutical Industry:
5-Chlorooxindole is used as a starting material for the preparation of tenidap sodium, a pharmaceutical drug candidate. It plays a crucial role in the synthesis process, contributing to the development of new medications.
Used in Anticancer Applications:
5-Chlorooxindole is used in the preparation of novel GSK-3β inhibitors, which are anticancer agents. These inhibitors target the glycogen synthase kinase-3 beta (GSK-3β) enzyme, which is involved in various cellular processes and has been implicated in the development and progression of cancer.
Used in Analytical Chemistry:
5-Chloro-2-oxindole (5-Chlorooxindole) is utilized for the quantitation of 5-chloro-2-oxindole, along with all of its potential positional isomers, using a single, highly specific, normal-phase chromatographic system. This application highlights its importance in the field of analytical chemistry for the accurate identification and quantification of related compounds.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1279, 1988 DOI: 10.1002/jhet.5570250501

InChI:InChI=1/C8H4ClNO/c9-6-1-2-7-5(3-6)4-8(11)10-7/h1-4H

Upstream product

• 65816-14-0 1-methoxyindolin-2-one 
• 129822-41-9 (4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 18108-55-9 1,3-dihydro-1-hydroxyindole-2-one 
• 1422148-82-0 2-(2-bromo-5-chlorophenyl)acetamide 
• 1351706-37-0 N-(2-iodo-4-chlorophenyl)-4-methylbenzenesulfonamide 
• 2593-90-0 2-(3-chlorophenyl)acetyl hydroxamic acid 
• 1878-65-5 3-chlorophenylacetic acid 
• 59-48-3 2-oxoindole 
• 71-55-6 1,1,1-trichloroethane 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 623-48-3 ethyl iodoacetae 
• 13939-06-5 molybdenum hexacarbonyl 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 

Downstream Products

• 113423-48-6 3,3-Dibromo-5-chloroindol-2(3H)-one 
• 1165901-97-2 3-(4-chlorobenzyl)-5-chloro-indolin-2-one 
• 1165901-92-7 3-benzyl-5-chloro-indolin-2-one 
• 120210-48-2 tenidap 
• 255712-65-3 5-chloro-1-phenoxycarbonyl-2-(thenoyloxy)indole 
• 255712-72-2 (Z)-5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 

Relevant articles and documents

Attempted synthesis of a Tenidap isomer and formation of an unexpected stable water adduct

An attempt to synthesize the Tenidap isomer 13 was performed starting from 2-ethoxy-5-chloroindole (9). The acylation and carbamoylation reactions of 9 led to the expected intermediate 12, however the hydrolysis of 12 in acidic or alkaline media did not y

Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate

A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.

Direct Superacid-Promoted Difluoroethylation of Aromatics

Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.