2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone

Name: 2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone
Brand: ChemScene
Availability: InStock
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CAS No. 57583-53-6
Cat. No. CS-0186523
Purity≥98%
MDL No.None

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2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone|CS-0186523

Structure of 57583-53-6

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General Information

CAS No. 57583-53-6
Cat. No. CS-0186523
Purity ≥98%
MDL No. None
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₄N₂O₆
Molecular Weight 248.15
Synonym(s) N,N'-Dihydroxypyromellitimide
SMILES C1=C2C(=CC3=C1C(=O)N(C3=O)O)C(=O)N(C2=O)O

Description

This electron-deficient heterocycle features four carbonyl groups arranged for enhanced reactivity in C–H functionalization. The two hydroxyl substituents at the 2- and 6-positions enable intramolecular hydrogen bonding, stabilizing reactive intermediates. Designed for use in advanced synthetic sequences requiring high regiocontrol.

Application

2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone serves as a versatile heterocyclic building block for the synthesis of complex polycyclic scaffolds. Its four ketone functionalities and phenolic hydroxyl groups enable sequential functionalization and serve as handles for derivatization via condensation, reduction, or metal-catalyzed coupling reactions. The molecule exhibits bench stability and facilitates purification by crystallization, making it suitable for use in medicinal chemistry campaigns targeting kinase inhibitors and other bioactive compounds.

Synthesis

Route1
- 89-32-7
- ~71%
- In-stock
  
  57583-53-6
References
- DAICEL CHEMICAL INDUSTRIES, LTD. Patent: EP1757583 A1, 2007 ; Location in patent: Page/Page column 16 ;
Route2
- In-stock
  
  89-05-4
- 89-32-7
- ~%
- In-stock
  
  57583-53-6
References
- DAICEL CHEMICAL INDUSTRIES, LTD. Patent: EP1862442 A1, 2007 ; Location in patent: Page/Page column 17 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 118.6
LogP -1.613
H_Acceptors 8
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Material Science Polymer Materials Macromolecular Monomer

Chemical Synthesis Synthetic Reagents Oxidation Oxidants (Other)

Key Words

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2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone

CAS No. 57583-53-6

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