1677-48-1

Basic information

• Product Name: 5,6-dichloro-1H-indole-2,3-dione
• Synonyms: 5,6-Dichloroindoline-2,3-dione
• CAS NO: 1677-48-1
• Molecular Formula: C₈H₃Cl₂NO₂
• Molecular Weight: 216.02
• Mol File: 1677-48-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 273-275℃
• Appearance: /
• Density: 1.643 g/cm³
• Refractive Index: 1.637
• Storage Temp.: 2-8°C
• PKA: 7.63±0.20(Predicted)
• CAS DataBase Reference: 5,6-dichloro-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dichloro-1H-indole-2,3-dione(1677-48-1)
• EPA Substance Registry System: 5,6-dichloro-1H-indole-2,3-dione(1677-48-1)

Safety Data

• Hazardous Substances Data: 1677-48-1(Hazardous Substances Data)

Usage

General Description

5,6-dichloro-1H-indole-2,3-dione is a chemical compound that belongs to the class of indole derivatives. It is a yellow solid with a molecular formula C8H3Cl2NO2 and a molecular weight of 218.02 g/mol. 5,6-dichloro-1H-indole-2,3-dione is often used in organic synthesis and as a building block for the preparation of various pharmaceuticals and agrochemicals. Its derivatives have been studied for their potential biological activities, including anti-inflammatory, antioxidant, and anti-cancer properties. 5,6-dichloro-1H-indole-2,3-dione is also known for its light and heat sensitivity, and should be handled and stored with care. Overall, this compound plays a significant role in the field of medicinal and agricultural chemistry, and continues to be of interest for further research and development.

InChI:InChI=1/C8H3Cl2NO2/c9-4-1-3-6(2-5(4)10)11-8(13)7(3)12/h1-2H,(H,11,12,13)

Upstream product

• 6341-92-0 6-chloroisatin 
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• 1081809-48-4 (2E)-N-(3,4-dichlorophenyl)-2-hydroxyimino-acetamide 
• 71293-59-9 5,6-dichloroindol-2-one 

Downstream Products

• 20776-61-8 2-amino-4,5-dichloro-benzoic acid 
• 865488-72-8 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide 
• 352278-23-0 5,6-dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one 
• 6958-39-0 6,7-dichloroquinazolin-4(3H)-one 
• 113525-09-0 2-(carboxymethyl-amino)-4,5-dichloro-benzoic acid 

Relevant articles and documents

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.

Synthesis and antifungal activity of 1-aminomethyl-3-{4- (chlorobenzyloxy) benzoylhydrazono}-4, 5/5, 6-dichloroindolin-2- ones

3-{4-(Chlorobenzyloxy) benzoylhydrazono}-4,5/5,6-dichloroindolin-2-ones 1a,b-5a,b, were synthesized by the condensation of 4-(chlorobenzyloxy) benzoylhydrazines and 4, 5/5, 6-dichloroindolin-2,3-diones. Compounds 1a,b-5a,b when subjected to Mannich reaction with secondary heterocyclic amines in the presence of formaldehyde, furnished 1-aminomethyl-3-{4-(chlorobenzyloxy) benzoylhydrazono}-4, 5/5, 6-dichloroindolin-2- ones 6a,b-20a,b. The structures of the compounds have been established by means of spectral (IR and 1H NMR) and elemental analysis. The compounds have been screened for their antifungal potential against human pathogenic fungi.