4067-01-0

Basic information

• Product Name: 1-O-TOLYL-PYRROLE-2,5-DIONE
• Synonyms: 1-(2-methylphenyl)-1h-pyrrole-5-dione;n-(o-methylphenyl)maleimide;n-2-tolylmaleimide;n-o-tolyl-maleimid;N-(O-TOLYL)MALEIMIDE;N-(2-METHYLPHENYL)MALEIMIDE;TIMTEC-BB SBB000264;1-O-TOLYL-PYRROLE-2,5-DIONE
• CAS NO: 4067-01-0
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Mol File: 4067-01-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 70-71 °C
• Boiling Point: 311.4 °C at 760 mmHg
• Flash Point: 139.3 °C
• Appearance: /
• Density: 1.277 g/cm³
• Vapor Pressure: 0.000565mmHg at 25°C
• Refractive Index: 1.615
• PKA: -0.13±0.20(Predicted)
• CAS DataBase Reference: 1-O-TOLYL-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-TOLYL-PYRROLE-2,5-DIONE(4067-01-0)
• EPA Substance Registry System: 1-O-TOLYL-PYRROLE-2,5-DIONE(4067-01-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 4067-01-0(Hazardous Substances Data)

Usage

General Description

1-O-Tolyl-pyrrole-2,5-dione is a chemical compound that falls under the category of organopalladium compounds, which are class of organometallic compounds containing a chemical bond between carbon and palladium. This particular chemical prominently features in organic chemistry research. Its structure includes a pyrrole-2,5-dione or succinimide ring, which makes it useful in several synthetic applications due to its propensity to act as a bi-functional linker. Due to its complex nature and specific properties, 1-O-Tolyl-pyrrole-2,5-dione is primarily used in research and development labs for the synthesis of other organic compounds.

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

Upstream product

• 95-53-4 o-toluidine 
• 3052-50-4 monomethyl maleate 
• 53616-19-6 (2-methylphenyl)maleamic acid 
• 67-56-1 methanol 
• 37902-59-3 N-o-tolyl-maleamic acid 
• 72889-88-4 (Z)-3-o-Tolylcarbamoyl-acrylic acid methyl ester 
• 108-31-6 maleic anhydride 

Downstream Products

• 1331731-60-2 (1R,3S,3aR,6aS)-methyl 4,6-dioxo-3-phenyl-5-(o-tolyl)octahydropyrrolo-[3,4-c]pyrrole-1-carboxylate 
• 331946-77-1 C₂₆H₂₁NO₃ 
• 1312543-92-2 C₂₆H₂₇NO₂ 
• 1264932-09-3 ethyl 9,11-dioxo-10-(o-tolyl)-6,9,10,11-tetrahydro-5H-pyrrolo[3',4':3,4] pyrrolo[2,1-a]isoquinoline-8-carboxylate 
• 72889-88-4 (Z)-3-o-Tolylcarbamoyl-acrylic acid methyl ester 
• 342417-65-6 4,6-dioxo-5-o-tolyl-1,3a,4,5,6,6a-hexahydro-pyrrolo[3,4-c]pyrazole-3-carboxylic acid methyl ester 

Relevant articles and documents

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.

Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite

A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cycloadditions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N′-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.

Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero)aromatics in batch and continuous flow

Trifluoromethylation of olefins and (hetero)aromatics with sodium triflinate as CF3 source and readily accessible benzophenone derivatives as photosensitisers has been developed in batch and flow. The use of an iridium-based photocatalyst enables the trifluoromethylation to proceed under visible light irradiation.