520-03-6

Basic information

• Product Name: N-PHENYLPHTHALIMIDE
• Synonyms: 2-PHENYL-ISOINDOLE-1,3-DIONE;N-PHENYLPHTHALIMIDE;PHTHALANIL;1H-Isoindole-1,3(2H)-dione, 2-phenyl-;1H-Isoindole-1,3(2H)-dione,2-phenyl-;2-Phenyl-1,3-isoindoledione;2-Phenyl-1,3-isoindolinedione;2-Phenyl-1H-isoindole-1,3(2H)-dione
• CAS NO: 520-03-6
• Molecular Formula: C₁₄H₉NO₂
• Molecular Weight: 223.23
• EINECS: 208-282-9
• Product Categories: Heterocyclic Compounds;Derivatives of phthalimide;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 520-03-6.mol
• Article Data: 188

Chemical Properties

• Melting Point: 204-207 °C(lit.)
• Boiling Point: 364.52°C (rough estimate)
• Flash Point: 182.6 °C
• Appearance: white crystalline powder
• Density: 1.1814 (rough estimate)
• Vapor Pressure: 2.99E-06mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: 2-8°C
• PKA: -0.54±0.20(Predicted)
• CAS DataBase Reference: N-PHENYLPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENYLPHTHALIMIDE(520-03-6)
• EPA Substance Registry System: N-PHENYLPHTHALIMIDE(520-03-6)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• RTECS: TI5635800
• Hazardous Substances Data: 520-03-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C14H9NO2/c16-13-11-8-4-5-9-12(11)14(17)15(13)10-6-2-1-3-7-10/h1-9H

Upstream product

• 110-86-1 pyridine 
• 85-44-9 phthalic anhydride 
• 582-61-6 benzoyl azide 
• 4870-16-0 N-anilinophthalimide 
• 16497-41-9 N,N'-diphenylphthalamide 
• 64-19-7 acetic acid 
• 7438-81-5 2-benzhydryl-2-nitro-indan-1,3-dione 
• 62-53-3 aniline 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 102-08-9 N,N-diphenylthiourea 
• 4727-29-1 phthalanilic acid 
• 77-78-1 dimethyl sulfate 
• 2439-85-2 N-bromophthalimide 
• 71-43-2 benzene 

Downstream Products

• 40101-60-8 2-(4-benzoylphenyl)-1H-isoindole-1,3(2H)-dione 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 62-53-3 aniline 
• 2142-03-2 2-p-tolylisoindoline-1,3-dione 
• 1026024-40-7 2-phenyl-3,4-dipropylisoquinolin-1(2H)-one 
• 1875-48-5 N-aminophthalamide 
• 132869-05-7 4-Amino-2-(2-carboxyphenyl)quinoline Hydrochloride 
• 127935-29-9 6-(4-Benzyl-piperazin-1-ylmethyl)-isoindolo[2,1-a]quinoline-5,11-dione 
• 132868-93-0 6,6a-Dihydro-5-(phenoxycarbonyloxy)isoindolo<2,1-a>quinolin-11(5H)-one 
• 127935-25-5 6-(N-Methylbenzylaminomethyl)isoindolo<2,1-a>quinoline-5,11(5H)-dione 
• 127935-24-4 6-(Benzylaminomethyl)isoindolo<2,1-a>quinoline-5,11(5H)-dione 
• 88460-50-8 ethyl 2-(3-oxo-2-phenylisoindolin-1-yl)acetate 
• 127935-38-0 2,3-Dihydro-3-oxo-2-phenyl-1H-isoindole-1-acetyl Chloride 
• 88460-51-9 2,3-Dihydro-3-oxo-2-phenyl-1H-isoindole-1-acetic Acid 

Relevant articles and documents

Defined Palladium-Phthalimidato Catalysts for Improved Oxidative Amination

New palladium(II)-phthalimidato complexes have been synthesized, isolated, and structurally characterized. As demonstrated from over 30 examples, they constitute superior catalysts for oxidative amination reactions of alkenes with phthalimide as the nitrogen source. This work streamlines vicinal difunctionalization of alkenes and provides access to significantly improved and experimentally simplified synthetic protocols.

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Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes - An efficient one pot syntheses of dibenz[de,g]-(2H)-isoquinoline-4, 6-dione derivatives

Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes afforded the corresponding dibenz[de,g]-(2H)-isoquinoline-4,6-dione derivatives in moderate to high yields via a reaction sequence involving [2+2] photocycloaddition, ring opening rearrangement of the oxetene intermediate and dehydrogenative cyclization in one pot. (C) 2000 Elsevier Science Ltd.

Mechanistic Studies of Ullmann-Type C–N Coupling Reactions: Carbonate-Ligated Copper(III) Intermediates

In Ullmann-type C?N coupling reactions, the involvement of CuIII species has been proposed many times on the basis of the oxidative addition–reductive elimination (OA-RE) path for these reactions, but actual species could not be traced in experimental studies. In the C?N coupling reactions, carbonate and phosphate were considered widely as bases. In the present study, Cu-mediated C?N coupling reactions of aryl halides and NuNH (amide and imide) were investigated extensively, and we provide direct spectroscopic evidence of actual CuIII species. For the first time, we reveal that carbonate and phosphate ions act as bidentate ligands as well as a base in the catalytic cycle, and thus the actual intermediate species is a carbonate- or phosphate-ligated, distorted octahedral CuIII complex. Our experimental and computational studies have strengthened the hypothesis that these reactions follow an OA-RE path.

Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst

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A phosphonium ylide as a visible light organophotoredox catalyst

A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.

High-throughput tandem-microwell assay for ammonia repositions FDA-Approved drugs to inhibit Helicobacter pylori urease

To date, little attempt has been made to develop new treatments for Helicobacter pylori (H. pylori), although the community is aware of the shortage of treatments for H. pylori. In this study, we developed a 192-tandem-microwell-based high-throughput assay for ammonia that is a known virulence factor of H. pylori and a product of urease. We could identify few drugs, that is, panobinostat, dacinostat, ebselen, captan, and disulfiram, to potently inhibit the activity of ureases from bacterial or plant species. These inhibitors suppress the activity of urease via substrate-competitive or covalent-allosteric mechanism, but all except captan prevent the antibiotic-resistant H. pylori strain from killing human gastric cells, with a more pronounced effect than acetohydroxamic acid, a well-known urease inhibitor and clinically used drug for the treatment of bacterial infection. This study offers several bases for the development of new treatments for urease-containing pathogens and to study the mechanism responsible for the regulation of urease activity.