4,6-Dichloroindoline-2,3-dione

4,6-Dichloroindoline-2,3-dione - Names and Identifiers

Name	4,6-DICHLORO-1H-INDOLE-2,3-DIONE
Synonyms	4,6-Dichloroisatin 4,6-DICHLORO-1H-INDO 4,6- twoisatin chloride 4,6-Dichloroindole-2,3-dione 4,6-Dichloroindoline-2,3-dione 4,6-DICHLORO-1H-INDOLE-2,3-DIONE 4,6-dichloro-2,3-dihydro-1H-indole-2,3-dione (3E)-3-[(4-propan-2-ylphenyl)methylidene]-2-pyrrolidinone
CAS	18711-15-4
InChI	InChI=1/C8H3Cl2NO2/c9-3-1-4(10)6-5(2-3)11-8(13)7(6)12/h1-2H,(H,11,12,13)

4,6-Dichloroindoline-2,3-dione - Physico-chemical Properties

Molecular Formula	C8H3Cl2NO2
Molar Mass	216.02
Density	1.643±0.06 g/cm3 (20 ºC 760 Torr)
Melting Point	260.5-261℃
Appearance	Yellow powder
pKa	8.59±0.20(Predicted)
Storage Condition	Sealed in dry,Room Temperature
Refractive Index	1.637

4,6-Dichloroindoline-2,3-dione - Reference Information

application

4, 6-dichloroisatin can be used as an intermediate in pharmaceutical and chemical synthesis. For example, 2-amino -4,6-dichlorobenzoic acid is prepared by adding hydrogen peroxide (28% v/v,10 ml) in batches to a solution of 4,6-dichloroisatin (5.0g,23.1mmol) in 75 mL1NNaOH(aq) at room temperature. After stirring for 2 hours, filter the reaction mixture to remove insoluble dark brown solids. The filter is then carefully acidified by concentration to pH2. Hydrochloric acid. The formed yellow precipitate is collected, washed with water and dried in vacuum. The target compound 2-amino -4, 6-dichlorobenzoic acid (3.90g,82%) is obtained by recrystallization from benzene, which is an ivory solid

Preparation

Add N-(3, 5-dichlorophenyl)-2-hydroxyimino-acetamide (10.0g,42.9mmol) slowly into concentrated HCl. Sulfuric acid (50mL) was added to the ice bath. At this time, the temperature of the reaction mixture is kept below 50°C. After the addition is complete, the dark solution is heated at 90°C for 10 minutes. After cooling the obtained to room temperature, pour the reactants in ice with 10 times the volume of the reactants and stir vigorously for 1 hour. The insoluble solids formed in the above steps are collected, washed with water, and dried in vacuum to obtain the target compound 4, 6-dichloro-1H-indole -2, 3-dione (4, 6-dichloroindigo)(8.90g,96%), which is an orange solid

Last Update：2024-04-10 22:29:15