52726-96-2

Basic information

• Product Name: 1-(phenylamino)-1H-pyrrole-2,5-dione
• CAS NO: 52726-96-2
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.1827
• Mol File: 52726-96-2.mol

Chemical Properties

• Boiling Point: 317.1°C at 760 mmHg
• Flash Point: 145.6°C
• Density: 1.436g/cm³
• Vapor Pressure: 0.000392mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: 1-(phenylamino)-1H-pyrrole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(phenylamino)-1H-pyrrole-2,5-dione(52726-96-2)
• EPA Substance Registry System: 1-(phenylamino)-1H-pyrrole-2,5-dione(52726-96-2)

Safety Data

• Hazardous Substances Data: 52726-96-2(Hazardous Substances Data)

Usage

Type of Compound

Heterocyclic compound

Structure

Contains a pyrrole ring and a maleimide group

Usage

a. Organic synthesis
b. Building block for complex molecules

Chemical Reactivity

a. Participates in Diels-Alder reactions
b. Participates in Michael addition reactions
c. Participates in cycloaddition reactions

Applications

a. Development of pharmaceuticals
b. Development of agrochemicals

Safety Precautions

Handle with care due to potential hazards and health risks

Upstream product

• 108-31-6 maleic anhydride 
• 100-63-0 phenylhydrazine 
• 6936-36-3 N-(phenylamino)maleiamic acid 

Relevant articles and documents

Tailoring the substitution pattern of Pyrrolidine-2,5-dione for discovery of new structural template for dual COX/LOX inhibition

Dual inhibition of the enzymatic pathways of cyclooxygenases (COX-1/COX-2) and lipoxygenase (LOX) is a rational approach for developing more efficient and safe anti-inflammatory agents. Herein, dual inhibitors of COX and LOX for the management of inflammation are reported. The structural modifications of starting pyrrolidine-2,5-dione aldehyde derivatives resulted in two structurally diverse families (Family A & B). Synthesized derivatives from both Families displayed preferential COX-2 affinity in submicromolar to nanomolar ranges. Disubstitution pattern of the most active series of compounds having N-(benzyl(4-methoxyphenyl)amino moiety presents a new template that is mimic to the diaryl pattern of traditional COX-2 inhibitors. Compound 78 with IC50 value of 0.051 ± 0.001 μM emerged as the most active compound. Highly potent COX-2/5-LOX inhibitors have also demonstrated appreciable in-vivo anti-inflammatory activity through carrageenan induced paw edema test. Moreover, the involvement of histamine, bradykinin, prostaglandin, and leukotriene mediators to adjust the inflammatory response were also studied. Apart from COX inhibition, sulfonamide is considered an important template for carbonic anhydrase inhibition. Hence, we also evaluated six sulfonamide derivatives for off-target in-vitro bovine carbonic anhydrase-II inhibition. Biological results were finally rationalized by docking simulations. Typically, most active COX-2 inhibitors interact with the amino acid residues responsible for the COX-2 selectivity.

Homo and copolymerization of N-(phenylamino)maleimide: Synthesis and characterization

Free radical homopolymerization of N-(phenylamino)maleimide (N-PAMI) and copolymerization with methyl methacrylate (MMA) were performed at 65°C with AIBN as initiator in THF. The molecular weights of polymers were determined by gel permeation chromatograp

An alumina-catalyzed Michael addition of mercaptans to N-anilinomaleimides and its application to the solution-phase parallel synthesis of libraries

A novel strategy for the synthesis of 3-sulfanylsubstituted 1-(arylamino)-pyrrolidine-2,5-dione derivatives via the alumina-catalyzed Michael addition of mercaptans to N-anilinomaleimides is described. The utilization of alumina in the synthesis offers important advantages such as good yields, convenience and mild conditions.