59648-09-8

Basic information

• Product Name: 1H-Pyrrole-2,5-dione, 1-(4-chlorophenyl)-3-methyl-
• CAS NO: 59648-09-8
• Molecular Formula: C11H8ClNO2
• Molecular Weight: 221.643
• Mol File: 59648-09-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-2,5-dione, 1-(4-chlorophenyl)-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2,5-dione, 1-(4-chlorophenyl)-3-methyl-(59648-09-8)
• EPA Substance Registry System: 1H-Pyrrole-2,5-dione, 1-(4-chlorophenyl)-3-methyl-(59648-09-8)

Safety Data

• Hazardous Substances Data: 59648-09-8(Hazardous Substances Data)

Upstream product

• 3120-04-5 3-methyl-1-phenylpyrrole-2,5-dione 
• 80818-24-2 (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 
• 80818-23-1 (Z)-(4-(4-chlorophenylamino)-2-methyl-4-oxo)but-2-enoic acid 
• 106-47-8 4-chloro-aniline 
• 616-02-4 citraconic acid anhydride 

Downstream Products

• 25998-50-9 1-(4-chlorophenyl)-3-methylpyrrolidine-2,5-dione 
• 1451750-80-3 (3R)-(+)-methyl-N-(4'-chlorophenyl)succinimide 
• 106-47-8 4-chloro-aniline 

Relevant articles and documents

Visible light mediated cyclization of tertiary anilines with maleimides using nickel(II) oxide surface-modified titanium dioxide catalyst

Surface-modified titanium dioxides by highly dispersed NiO particles have an extended absorption in the visible light region and a reduced hole-electron pair recombination than unmodified TiO2. They have now been successfully applied as highly active heterogeneous photocatalysts in the visible light mediated direct cyclization of tertiary anilines with maleimides to give tetrahydroquinoline products in moderate to high yields at ambient temperature. In contrast with unmodified titanium dioxide catalysts that are conventionally used in a stoichiometric amount in combination with UVA light, only a catalytic amount (1 mol %) of the surface-modified TiO2 catalyst is needed along with visible light to efficiently catalyze the reaction. Compared with transition-metal complexes such as Ru(bpy)3Cl2 or Ir(ppy)2(dtbbpy)PF6, advantages of these surface-modified titanium dioxides as photocatalyst include high catalytic activity, low cost, ease of recovering, and being able to be used for at least nine times without significant decay of catalytic activity.

Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4- (arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et 3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio. TUeBITAK, 2012.