66195-04-8

Basic information

• Product Name: 3-benzylpyrrolidine-2,5-dione
• CAS NO: 66195-04-8
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.2105
• Mol File: 66195-04-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 381.3°C at 760 mmHg
• Flash Point: 170.7°C
• Density: 1.212g/cm³
• Vapor Pressure: 5.13E-06mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 3-benzylpyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzylpyrrolidine-2,5-dione(66195-04-8)
• EPA Substance Registry System: 3-benzylpyrrolidine-2,5-dione(66195-04-8)

Safety Data

• Hazardous Substances Data: 66195-04-8(Hazardous Substances Data)

Upstream product

• 541-59-3 maleiimide 
• 108-88-3 toluene 
• 100-52-7 benzaldehyde 
• 14063-01-5 3-benzylidenepyrrolidin-2,5-dione 
• 123-56-8 Succinimide 
• 100-44-7 benzyl chloride 
• 36092-42-9 2-benzylsuccinic acid 
• 770-09-2 benzyltrimethylsilane 

Downstream Products

• 170304-83-3 3-benzylpyrrolidine 

Relevant articles and documents

Synthesis and evaluation of anticonvulsant properties of new N-Mannich bases derived from 3-(1-phenylethyl)- and 3-benzyl-pyrrolidine-2,5-dione

Two series of new derivatives of pyrrolidine-2,5-dione were synthesized and evaluated for their anticonvulsant properties. Initial screening for their anticonvulsant properties was performed in mice after intraperitoneal administration, using the maximal

Decatungstate photocatalyzed benzylation of alkenes with alkylaromatics

The direct benzylation of electrophilic al-kenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5 M lithium perchlorate). The reaction has been extended to ring-substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (p-cymene, 4-methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the deca-tungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/ electron transfer processes.

Synthesis of succinimido[3,4-b]indane and 1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine-2,4-dione by sequential alkylation and intramolecular arylation of enolates derived from N,N,N'N'-tetramethylbutanediamides and N,N,N'N'-tetramethylpentanediamides

The tricyclic title compounds, 4 and 5, were synthesized by initial alkylation of the lithium monoenolates of N,N,N',N'-tetramethylbutanediamide (6) and N,N,N',N'-tetramethylpentanediamide (19) with 2-iodobenzyl chloride in liquid NH3 at -60°C to afford 2-(2-iodobenzyl)-N,N,N',N'-tetramethylbutanediamide (9) and 2-(2-iodobenzyl)-N,N,N',N'-tetramethylpentanediamide (20) in yields of 88 and 87%, respectively. Treatment of 9 with KNH2 in liquid NH3 resulted in formation and intramolecular arylation of the less-substituted α-enolate to produce trans-1,2-bis(N,N-dimethylcarboxamido)indane (10a) in 60% yield. Selective hydrolysis of 10a with aqueous Na2O2 gave trans-1-(N,N-dimethylcarboxamido)indane-2-carboxylic acid (17), which was then converted to bridged succinimide 4 by transformation to trans-1-(N,N-dimethylcarboxamido)indane-2-carboxamide (10c) followed by cyclization of this mixed primary/tertiary amide by means of NaH in refluxing THF. Treatment of 20 with KNH2 in liquid NH3 led to intramolecular arylation and accompanying ammonolysis to afford trans-1-(N,N-dimethylcarboxamido)-1,2,3,4-tetrahydronaphthalene-3-carboxamide (21b). Conversion of 21b to 5 was similarly effected by means of NaH. Experiments designed to test the mechanistic aspects of the intramolecular arylations provided evidence for competing aryne and SET pathways.