1631-28-3

Basic information

• Product Name: 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE
• Synonyms: WLN: T5VNVJ BR D1;IT 510;Maleimide, N-p-Tolyl-;N-(para-Tolyl)-maleimide;N-(p-Methylphenyl)maleimide;N-4-Tolylmaleimide;n-p-tolyl-maleimid;p-Tolylmaleimide
• CAS NO: 1631-28-3
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Mol File: 1631-28-3.mol
• Article Data: 55

Chemical Properties

• Melting Point: 149-150 °C
• Boiling Point: 333.2 °C at 760 mmHg
• Flash Point: 154.2 °C
• Appearance: /
• Density: 1.277 g/cm³
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: 2-8°C
• PKA: -0.29±0.20(Predicted)
• CAS DataBase Reference: 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE(1631-28-3)
• EPA Substance Registry System: 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE(1631-28-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1631-28-3(Hazardous Substances Data)

Usage

General Description

1-(4-Methylphenyl)-1H-pyrrole-2,5-dione, also known as 4-Methylphenyl-1H-pyrrole-2,5-dione or 4-methylphenylmaleimide, is a chemical compound with the molecular formula C11H9NO2. It is a yellowish solid that is insoluble in water but soluble in organic solvents. It is used as a reagent in organic synthesis and as a building block for the synthesis of various pharmaceuticals and agrochemicals. 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE is also known to exhibit antioxidant and radical scavenging properties, making it potentially useful in industrial and medicinal applications. It is important to handle this chemical with care as it may have toxic, irritant, and harmful effects if not used properly.

InChI:InChI=1/C11H9NO2/c1-8-2-4-9(5-3-8)12-10(13)6-7-11(12)14/h2-7H,1H3

Upstream product

• 65344-80-1 methyl p-methylmaleanilate 
• 3052-50-4 monomethyl maleate 
• 106-49-0 p-toluidine 
• 108-31-6 maleic anhydride 
• 15485-32-2 N-(4-chlorobenzylidene)-4-toluidine 
• 2272-45-9 benzal-p-toluidine 
• 24870-11-9 4-methylmaleanilic acid 
• 541-59-3 maleiimide 
• 557-24-4 maleamic acid 
• 55818-45-6 methyltriphenylphosphonium 4-methylbenzenesulfonate 
• 38046-98-9 3-chloro-1-(4-methylphenyl)pyrrolidine-2,5-dione 
• 67-56-1 methanol 
• 37904-03-3 3-p-tolylcarbamoyl-acrylic acid 

Downstream Products

• 3120-18-1 6,6-diphenyl-3-p-tolyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 3191-81-9 3-p-tolyl-spiro[3-aza-bicyclo[3.1.0]hexane-6,9'-fluorene]-2,4-dione 
• 89143-14-6 1'-p-Tolyl-[1,3']bipyrrolidinyl-2',5'-dione 
• 127797-99-3 C₂₆H₂₂N₂O₂ 
• 2142-03-2 2-p-tolylisoindoline-1,3-dione 

Relevant articles and documents

Diels-Alder reactions of five-membered heterocycles containing one heteroatom

Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 °C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 °C to give 4,7-dimethyl-2-p-tolylisoindoline-1,3-dione (6).

1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids

A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.