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

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

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 
• 60437-34-5 2-(2-amino-4-methyl-7-oxo-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-6-yl)-N-p-tolyl-acetamide 
• 41379-04-8 4,7-bis-benzo[1,3]dioxol-5-yl-1,3,9-trioxo-2-p-tolyl-2,3,3a,4,5,6,7,8,9,9b-decahydro-1H-benzo[e]isoindole-8-carboxylic acid ethyl ester 
• 57703-48-7 4,9-diphenyl-2-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 57703-54-5 6,7-dimethyl-2,4,9-tri-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 54819-65-7 2-Iminothiazolid-4-on-5-acet-(4-methylanilid) 
• 70464-66-3 5-p-tolyl-3-(2,4,6-trimethyl-phenyl)-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 54819-59-9 2-(4-Methoxyphenyl)-iminothiazolid-4-on-5-acet-(4-methylanilid) 
• 89143-14-6 1'-p-Tolyl-[1,3']bipyrrolidinyl-2',5'-dione 
• 89143-26-0 3-piperidin-1-yl-1-p-tolyl-pyrrolidine-2,5-dione 
• 118617-08-6 5-((3aS,3cS,6aR,8aR)-1,3,4,6-Tetraoxo-2,5-di-p-tolyl-octahydro-7,8-dioxa-2,5,7a-triaza-dicyclopenta[a,f]pentalen-3b-yl)-pentanenitrile 
• 78817-63-7 5-Acetyl-4-phenyl-2-p-tolyl-3a,11c-dihydro-4H-6-oxa-2,11b-diaza-cyclopenta[c]phenanthrene-1,3,7-trione 
• 106369-04-4 (3aS,6aR)-2-Methyl-4,6-dioxo-5-p-tolyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid ethyl ester 

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.

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.