61394-93-2

Basic information

• Product Name: 4-NITRO-2,3-DIOXYINDOLE
• Synonyms: 4-NITRO-2,3-DIOXYINDOLE;4-Nitroindoline-2,3-dione;skln-0055
• CAS NO: 61394-93-2
• Molecular Formula: C₈H₄N₂O₄
• Molecular Weight: 192.13
• Mol File: 61394-93-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.609 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-NITRO-2,3-DIOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-2,3-DIOXYINDOLE(61394-93-2)
• EPA Substance Registry System: 4-NITRO-2,3-DIOXYINDOLE(61394-93-2)

Safety Data

• Hazardous Substances Data: 61394-93-2(Hazardous Substances Data)

Usage

General Description

4-NITRO-2,3-DIOXYINDOLE is a chemical compound that belongs to the family of indole derivatives. It is characterized by the presence of a nitro group and two oxygen atoms attached to the indole ring. 4-NITRO-2,3-DIOXYINDOLE has been studied for its potential applications in the field of organic chemistry and material science. Its unique structure and properties make it a valuable building block for the synthesis of complex molecules and materials with specific functionalities. Additionally, 4-NITRO-2,3-DIOXYINDOLE has garnered interest for its potential biological activities and is being investigated for its pharmacological properties. Overall, this chemical compound holds promise for various applications in research and industry.

Synthetic route

indole-2,3-dione (91-56-5) → 4-nitro-1H-indole-2,3-dione (61394-93-2)

Conditions	Yield
With copper(II) nitrate In water; acetic acid for 0.025h; Nitration; microwave irradiation;	68%

3-nitroisonitrosoacetanilide (17122-61-1) → 4-nitro-1H-indole-2,3-dione (61394-93-2)

Conditions	Yield
With sulfuric acid at 50 - 80℃; for 20.1667h;	26%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1,3-cylohexanedione (504-02-9) + malononitrile (109-77-3) → C17H12N4O5

Conditions	Yield
With NiO nanoparticles on the graphitic carbon nitride nanosheets In ethanol at 80℃; for 0.0333333h;	95%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + malononitrile (109-77-3) → C20H10N4O6

Conditions	Yield
With NiO nanoparticles on the graphitic carbon nitride nanosheets In ethanol at 80℃; for 0.0833333h;	93%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + p-toluidine (106-49-0) → -nitro-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione

Conditions	Yield
With Tau In water for 6.5h; Reflux; Green chemistry;	90%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + aniline (62-53-3) → C21H14N4O4

Conditions	Yield
With Tau In water for 6h; Reflux; Green chemistry;	89%

isatoic anhydride (118-48-9) + 4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-methoxy-aniline (104-94-9) → 3'-(4-methoxyphenyl)-4-nitro-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione

Conditions	Yield
With Tau In water for 6h; Reflux; Green chemistry;	88%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) + (RS)-4-thiazolidinecarboxylic acid (444-27-9, 19291-02-2, 34592-47-7, 45521-09-3) → C25H19N5O4S

Conditions	Yield
In ethanol; water for 3h; Reflux;	73%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) + rac-Pro-OH (609-36-9) → C26H21N5O4

Conditions	Yield
In ethanol; water for 3h; Reflux;	66%

4-nitro-1H-indole-2,3-dione (61394-93-2) + L-phenylalanine (63-91-2) + 3-(3-pyridinylmethylidene)-2-oxindole (3367-89-3) → C30H23N5O4

Conditions	Yield
With air In ethanol; water for 3h; Reflux;	35%

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-hydrazinobenzene-1-sulfonamide hydrochloride (17852-52-7, 27918-19-0) → 4-[N'-(4-nitro-2-oxo-1,2-dihydro-indol-3-ylidene)hydrazino]benzenesulfonamide

Conditions	Yield
In ethanol for 2h; Heating;	33%

4-nitro-1H-indole-2,3-dione (61394-93-2) → 4-[N'-(4-Nitro-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-benzenesulfonamide (222034-75-5, 388626-46-8)

Conditions	Yield
	33%

4-nitro-1H-indole-2,3-dione (61394-93-2) + acetophenone (98-86-2) → C17H14N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;	18%

3-indoxyl acetate (608-08-2) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → 4-nitroindirubin (1257060-34-6)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 65 - 70℃; for 3h;	15%

1'-naphthacetophenone (941-98-0) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → C21H16N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

1,4-benzodioxan-6-yl methyl ketone (2879-20-1) + 4-nitro-1H-indole-2,3-dione (61394-93-2) → C19H16N2O7

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-ethylacetophenone (937-30-4) → C19H18N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-chloroacetophenone (99-91-2) → C17H13ClN2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-bromoacetophenone (99-90-1) → C17H13BrN2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + para-methylacetophenone (122-00-9) → C18H16N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → C17H12Cl2N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(4-methoxyphenyl)ethanone (100-06-1) → C18H16N2O6

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 3',4'-dichloroacetophenone (2642-63-9) → C17H12Cl2N2O5

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → C19H18N2O7

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;

4-nitro-1H-indole-2,3-dione (61394-93-2) + 4-phenyl-semicarbazide (537-47-3) → C15H11N5O4 (1380571-03-8)

Conditions	Yield
With acetic acid In ethanol Microwave irradiation;

Upstream product

• 17122-61-1 3-nitroisonitrosoacetanilide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1380571-03-8 C₁₅H₁₁N₅O₄ 
• 222034-75-5 4-[N'-(4-Nitro-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-benzenesulfonamide 

Relevant articles and documents

Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid

The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.

Nitration of nitrogen heterocycles using microwaves

A comparative study of reaction time and yields for nitration of nitrogeneous heterocyclic compounds using Cu(NO3)2, KNO3 and NaNO3 under microwave irradiation as well as by conventional heating is reported.