57583-53-6

Basic information

• Product Name: 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone
• Synonyms: 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone;N,N'-Dihydroxypyromellitimide;N,N'-Dihydroxypyromellitimide;2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7-tetrone;2,6-dihydroxypyrrolo(3,4-f)isoindole-1,3,5,7(2h,6h)-tetrone
• CAS NO: 57583-53-6
• Molecular Formula: C₁₀H₄N₂O₆
• Molecular Weight: 248.15
• Mol File: 57583-53-6.mol

Chemical Properties

• Boiling Point: 687.2°Cat760mmHg
• Flash Point: 369.4°C
• Appearance: /
• Density: 2.261g/cm³
• Vapor Pressure: 7.93E-20mmHg at 25°C
• Refractive Index: 1.929
• Solubility: slightly sol. in Dimethylformamide
• PKA: 6.15±0.20(Predicted)
• CAS DataBase Reference: 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone(57583-53-6)
• EPA Substance Registry System: 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone(57583-53-6)

Safety Data

• Hazardous Substances Data: 57583-53-6(Hazardous Substances Data)

Usage

Uses

As of now, there is limited information available on the specific applications of 2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone. However, based on its chemical structure, it may have potential uses in the following areas:
Used in Chemical Synthesis:
2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone is used as a precursor in the synthesis of more complex molecules for [application reason]. Its structure may allow for further chemical reactions and modifications, making it a candidate for use in the development of new compounds.
Used in Research and Development:
2,6-dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone is used as a subject of study in research and development for [application reason]. Its obscure nature and limited research make it an interesting candidate for further investigation, potentially leading to new discoveries and applications in various fields.

InChI:InChI=1/C10H4N2O6/c13-7-3-1-4-6(10(16)12(18)8(4)14)2-5(3)9(15)11(7)17/h1-2,17-18H

Upstream product

• 89-32-7 Pyromellitic dianhydride 
• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 

Downstream Products

• 535952-46-6 2,6-bis(pentafluorobenzenesulfonyloxy)benzo[1,2-c:4,5-c'] dipyrrole-1,3,5,7(2H,6H)-tetrone 
• 535952-34-2 2,6-bis(3-trifluoromethylphenylsulfonyloxy)benzo[1,2-c:4,5-c']dipyrrole-1,3,5,7(2H,6H)-tetrone 
• 535952-37-5 2,6-diphenylsulphonyloxy-1H,3H,5H,7H-pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone 
• 1429225-57-9 4,9-di(4-methoxyphenyl)-1H,6H[1,2]oxazino[5,4-g][2,3]benzoxazine-1,6-dione 
• 1429225-60-4 4,6-di(4-methoxyphenyl)-1H,9H[1,2]oxazino[4,5-g][2,3]benzoxazine-1,9-dione 

Relevant articles and documents

High-efficient metal-free aerobic oxidation of aromatic hydrocarbons by N, N-dihydroxypyromellitimide and 1,4-diamino-2,3-dichloroanthraquinone

Metal-free organic catalytic system combining with N, N-dihydroxypyromellitimide (NDHPI) and 1,4-diamino-2,3-dichloroanthraquinone (DADCAQ) was developed for the selective oxidation of hydrocarbon. Being able to simultaneously show good catalytic activity for the oxidation of hydrocarbon and alcohol, NDHPI/DADCAQ was found to be efficient for the conversion of hydrocarbon to ketone. In addition, due to its specific molecular structure, NDHPI was found to be more stable and could supply a PIDNO (pyromellitimide N, N-dioxyl free radical) during the catalytic process. So, higher catalytic activity could be obtained than the famous NHPI even with only half usage, which resolved the problem of high usage (usually 10 mol%) for the organic N-OH compounds to some extent. With 5 mol% NDHPI and 1.25 mol% DADCAQ being used under the conditions of 110 °C and 0.3 MPa molecular oxygen for 7 h, high conversion of ethylbenzene (89.6%), tetralin (98.8%), indene (96.9%), and inert toluene (50.7%) could be selectively converted to the products of acetophenone (93.4%), α-tetralone (97.3%), 1-indanone (98.9%), and benzoic acid (92.4%), respectively.

Selective aerobic oxidation of toluene to benzaldehyde catalyzed by covalently anchored N-hydroxyphthalimide and cobaltous ions

Selective oxidation of toluene to benzaldehyde via dioxygen is of great significance industrially but suffers from a severely low selectivity due to a much higher reactivity of the desired product than the reactant. A combination of homogeneous N-hydroxyphthalimide (NHPI) and cobaltous ions was found active and selective for the transformation from toluene to benzaldehyde in the presence of hexafloropropan-2-ol. In this work, homogeneous NHPI was covalently anchored onto the surface of commercial mesoporous SiO2 to facilitate the separation and recovery of the catalyst, aiming at a possible industrial application. The grafting bonds were well confirmed by FT-IR, TGA and XP spectra, and the density of > N–OH groups anchored was up to 0.6 mmol/g in the immobilized NHPI catalysts. The resulting catalysts exhibited an excellent activity for selective oxidation of toluene to benzaldehyde, and there was no appreciable loss in catalytic activity observed after repeated evaluations, suggesting a promising prospect for its further investigation and possible application.

Kinetics of N-oxyl Radicals' Decay

N-oxyl radicals of various structures were generated by oxidation of corresponding N-hydroxy compounds with iodobenzene diacetate, [bis(trifluoroacetoxy)]iodobenzene, and ammonium cerium(IV) nitrate in acetonitrile. The decay rate of N-oxyl radicals follows first-order kinetics and depends on the structure of N-oxyl radicals, reaction conditions, and the nature of the solvent and oxidant. The values of the self-decay constants change within 1.4 × 10-4 s-1 for the 3,4,5,6-tetraphenylphthalimide-N-oxyl radical to 1.4 × 10-2 s-1 for the 1-benzotriazole-N-oxyl radical. It was shown that the rate constants of the phthalimide-N-oxyl radicalsê? self-decay with different electron-withdrawing or-donor substituents in the benzene ring are higher than that of the unsubstituted phthalimide-N-oxyl radical in most cases. The solvent effect on the process of phthalimide-N-oxyl radical self-decomposition was investigated. The dependence of the rate constants on the Gutmann donor numbers was shown.

USE OF ORGANIC OXYIMIDES AS FLAME RETARDANT FOR PLASTIC MATERIALS AND ALSO FLAME-RETARDANT PLASTIC MATERIAL COMPOSITION AND MOULDED PARTS PRODUCED THEREFROM

The present invention relates to the use of organic oxy imides as flame retardants for plastics. According to the present invention, a flame-retardant plastics composition is likewise specified, including an oxy imide as flame retardant. Additionally specified are mouldings produced from an inventive flame-retardant polymer composition.

PROCESS FOR OXIDATION OF ORGANIC COMPOUNDS

A method oxidizes an organic compound with oxygen in the presence of a catalyst, in which the catalyst contains a N-hydroxy- or N-(substituted oxy)-imide compound derivable from at least one selected from a target product, a reaction intermediate, and a reaction byproduct, and the catalyst is produced from at least one component selected from the target product, reaction intermediate, and reaction byproduct each formed as a result of the reaction and is used in the oxidation reaction so as to make up for a loss of the catalyst due to denaturation in the reaction. The method can easily and inexpensively make up for a loss of the catalyst denaturated in the course of reaction.

PROCESS FOR PRODUCING CYCLIC N-HYDROXYIMIDE COMPOUND

A cyclic polycarboxylic acid anhydride, a polycarboxylic acid, or a mixture of them is allowed to react with hydroxylamine or a salt thereof in an organic solvent under dewatering conditions to yield a corresponding cyclic N-hydroxyimide compound. The cyclic polycarboxylic acid anhydride can be, for example, succinic anhydride or glutaric anhydride. The polycarboxylic acid can be, for example, succinic acid, glutaric acid, or adipic acid. In this process, the reaction is preferably carried out using an organic solvent capable of undergoing azeotropy with water as all or part of a reaction solvent while removing water from the reaction system by azeotropy with the organic solvent. This process produces a cyclic N-hydroxyimide compound in a good yield from any of a cyclic polycarboxylic acid anhydride and a polycarboxylic acid.

BISIMIDE COMPOUND, ACID GENERATOR AND RESIST COMPOSITION EACH CONTAINING THE SAME, AND METHOD OF FORMING PATTERN FROM THE COMPOSITION

The present invention relates to a novel bisimide compound useful as an acid generator for a chemically amplified resist composition used in manufacturing of semiconductor element and the like or a raw material for synthesizing heat resistant polymers, an

N-Hydroxyphthalimides and Metal Cocatalysts for the Autoxidation of p-Xylene to Terephthalic Acid

N-Hydroxyphthalimide (NHPI) and its derivatives, such as 3-F-NHPI, 4-Me-NHPI, N-acetoxyphthalimide, and N,N-dihydroxypyromelitimide, were used as promoters with Co(OAc)2 catalyst for the autoxidation of p-xylene (pX) and other methyl arenes. All the promoters gave acceptable rates and yields of terephthalic acid. The initial reaction rates, measured by the rate of oxygen uptake, were analyzed by a rate equation in terms of [pX], [Co(II)], and [NHPI]. The metal cocatalysts Mn(II) and Ce(III) accelerated the reaction significantly at millimolar concentrations. The reaction occurs by a chain mechanism that involves formation of the phthalimide N-oxyl radical, PINO . (that is, R2NO.), which abstracts a hydrogen atom from the methyl group of p-xylene to form the carbon-centered radical ArCH2.. In a stepwise fashion, the sequence progresses through alcohol, aldehyde, and carboxylic acid; at each stage, C-H abstraction by PINO. is involved. A significant kinetic isotope effect on the overall oxidation of p-xylene was found, vi(H)/vi(D) = 3.4. The activity of the substituted NHPI promoters follows the order NHPI > 3-F-NHPI > 4-Me-NHPI, which can be interpreted in terms of kinetic stability of the corresponding PINO radical.