19077-60-2

Basic information

• Product Name: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE
• Synonyms: (1-p-ethoxyphenyl)-1h-pyrrole-5-dione;1-(4-ethoxyphenyl)maleimide;1-(p-ethoxyphenyl)-1h-pyrrole-2,5-dione;ephm;n-(p-ethoxyphenyl)-maleimid;N-(4-ETHOXYPHENYL)MALEIMIDE;ASISCHEM C66318;1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE
• CAS NO: 19077-60-2
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• Mol File: 19077-60-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 371.5 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: /
• Density: 1.272 g/cm³
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(19077-60-2)
• EPA Substance Registry System: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(19077-60-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 19077-60-2(Hazardous Substances Data)

Usage

General Description

1-(4-Ethoxyphenyl)-1H-pyrrole-2,5-dione is a chemical compound with the molecular formula C12H11NO3. It is a derivative of pyrrole-2,5-dione and contains an ethoxyphenyl group. 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE is commonly used in the production of pharmaceuticals and agrochemicals due to its diverse range of biological activities. It has been studied for its potential as an anti-inflammatory and anti-cancer agent, as well as for its ability to inhibit the growth of harmful microorganisms. Additionally, it has been investigated for its potential as a fluorescent dye and as a component in organic electronic devices. Its unique structure and versatile properties make it a valuable compound in various industries.

InChI:InChI=1/C12H11NO3/c1-2-16-10-5-3-9(4-6-10)13-11(14)7-8-12(13)15/h3-8H,2H2,1H3

Upstream product

• 156-43-4 4-Ethoxyaniline 
• 100122-11-0 1-(4-ethoxy-phenyl)-3-chloro-pyrrolidine-2,5-dione 
• 51992-13-3 N-(4-ethoxy-phenyl)-malamic acid 
• 108087-84-9 N-(4-ethoxy-phenyl)-maleamic acid 

Downstream Products

• 100122-11-0 1-(4-ethoxy-phenyl)-3-chloro-pyrrolidine-2,5-dione 
• 59256-45-0 N-(4-ethoxy-phenyl)-succinamic acid 
• 611-41-6 N-(4-ethoxy-phenyl)-succinimide 
• 374563-53-8 C₂₈H₂₀FNO₆ 
• 485395-11-7 C₂₉H₂₃NO₆ 
• 485395-10-6 C₂₈H₂₁NO₆ 
• 1197921-27-9 5-(4-ethoxyphenyl)-3-(3-nitrophenyl)-3a,4,6,6a-tetrahydro-4H,6H-pyrrolo[3,4-d]isoxazoline-4,6-dione 
• 106058-41-7 N-(4-ethoxy-phenyl)-aspartic acid-(4-ethoxy-phenylimide) 
• 106058-31-5 1-(4-Ethoxy-phenyl)-3-(4-methoxy-phenylamino)-pyrrolidine-2,5-dione 

Relevant articles and documents

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.