20871-03-8

Basic information

• Product Name: 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione
• Synonyms: 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione;5-amino-2-phenyl-1H-isoindole-1,3(2H)-dione
• CAS NO: 20871-03-8
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.2414
• Mol File: 20871-03-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione(20871-03-8)
• EPA Substance Registry System: 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione(20871-03-8)

Safety Data

• Hazardous Substances Data: 20871-03-8(Hazardous Substances Data)

Upstream product

• 5434-21-9 4-aminophthalic acid 
• 62-53-3 aniline 
• 51832-31-6 4-amino-phthalic acid dimethyl ester 
• 40392-27-6 4-nitro-N-phenylphthalimide 
• 53555-04-7 2-(4-chloro-phenyl)-5-nitro-isoindoline-1,3-dione 
• 5466-84-2 4-nitrophthalic anhydride 
• 610-27-5 4-nitrophthalic acid 
• 610-22-0 dimethyl 4-nitrophthalate 

Downstream Products

• 110050-47-0 5-(4-hydroxy-phenylazo)-2-phenyl-isoindoline-1,3-dione 
• 35014-20-1 5-(2-hydroxy-[1]naphthylazo)-2-phenyl-isoindoline-1,3-dione 
• 305359-20-0 N-(1,3-dioxo-2-phenylisoindolin-5-yl)isobutyramide 

Relevant articles and documents

Selective Synthesis of Primary Anilines from NH3 and Cyclohexanones by Utilizing Preferential Adsorption of Styrene on the Pd Nanoparticle Surface

Dehydrogenative aromatization is one of the attractive alternative methods for directly synthesizing primary anilines from NH3 and cyclohexanones. However, the selective synthesis of primary anilines is quite difficult because the desired primary aniline products and the cyclohexanone substrates readily undergo condensation affording the corresponding imines (i.e., N-cyclohexylidene-anilines), followed by hydrogenation to produce N-cyclohexylanilines as the major products. In this study, primary anilines were selectively synthesized in the presence of supported Pd nanoparticle catalysts (e.g., Pd/HAP, HAP=hydroxyapatite, Ca10(PO4)6(OH)2) by utilizing competitive adsorption unique to heterogeneous catalysis; in other words, when styrene was used as a hydrogen acceptor, which preferentially adsorbs on the Pd nanoparticle surface in the presence of N-cyclohexylidene-anilines, various structurally diverse primary anilines were selectively synthesized from readily accessible NH3 and cyclohexanones. The Pd/HAP catalyst was reused several times though its catalytic performance gradually declined.

Synthesis and anticonvulsant activity of some N-phenylphthalimides

The anticonvulsant potential of a series of N-phenylphthalimide derivatives has been screened in subcutaneous pentylenetetrazole seizure (scPTZ) and maximal electroshock seizure (MES) tests. Intraperitoneal 4-amino-N-phenylphthalimides were the most potent agents against MES in mice. Referring to the N-(2,6-dimethylphenyl)phthalimide structure, the order of anticonvulsant activity appears to correspond to the phthalimide ring substitution pattern of 4-amino > 4-nitro > 4-methyl; H > 3-nitro; 3-amino. The 4-amino-N-(2-methylphenyl)phthalimide displays an anti-MES ED50 of 47.61 μmol/kg with a protective index (PI) of 4.2. Oral administration to rats of the compounds found to be active in mice showed that the 4-amino-N-(2,6-dimethylphenyl)phthalimide is the most potent anti-MES agent in rats, exhibiting an ED50 of 25.2 μmol/kg and a PI greater than 75. Regarding the nature of the 2 and 6 substituents of the N-phenyl ring, the anticonvulsant efficiencies may be ordered as follows: 2,6-dimethyl > 2-methyl > 2-ethyl > 2-ethyl-6-methyl > 2,6-diethyl > unsubstituted phenyl ring. N-Phenylphthalimide derivatives seem to have great potential as candidate anticonvulsant drugs.