16082-71-6

Basic information

• Product Name: 2-(3-Chlorophenyl)-2H-isoindole-1,3-dione
• Synonyms: 2-(3-Chlorophenyl)-1,3-dihydro-2H-isoindole-1,3-dione;2-(3-Chlorophenyl)-1H-isoindole-1,3(2H)-dione;2-(3-Chlorophenyl)-2H-isoindole-1,3-dione;2-(3-Chlorophenyl)isoindoline-1,3-dione;N-(3-Chlorophenyl)phthalimide;N-(m-Chlorophenyl)phthalimide
• CAS NO: 16082-71-6
• Molecular Formula: C₁₄H₈ClNO₂
• Molecular Weight: 257.67
• Mol File: 16082-71-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 162 °C
• Boiling Point: 434.1±47.0 °C(Predicted)
• Appearance: /
• Density: 1.441±0.06 g/cm3(Predicted)
• PKA: -1.69±0.20(Predicted)
• CAS DataBase Reference: 2-(3-Chlorophenyl)-2H-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Chlorophenyl)-2H-isoindole-1,3-dione(16082-71-6)
• EPA Substance Registry System: 2-(3-Chlorophenyl)-2H-isoindole-1,3-dione(16082-71-6)

Safety Data

• Hazardous Substances Data: 16082-71-6(Hazardous Substances Data)

Upstream product

• 5406-21-3 2-[(3-chlorophenyl)aminocarbonyl]benzoic acid 
• 109949-63-5 2-(3-chlorophenyl)-2,3-dihydro-1H-isoindole 
• 670-54-2 ethenetetracarbonitrile 
• 3481-09-2 N-chlorophthalimide 
• 108-90-7 chlorobenzene 
• 1864-94-4 phenyl formate 
• 197141-50-7 N-(3-chlorophenyl)-o-iodobenzamide 
• 524-38-9 N-hydroxyphthalimide 
• 108-42-9 3-chloro-aniline 
• 88-67-5 2-Iodobenzoic acid 
• 201230-82-2 carbon monoxide 
• 13208-31-6 N_.N'-Di-(m-chlor-phenyl)-harnstoff 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 136918-14-4 phthalimide 

Downstream Products

• 79419-89-9 2-(3-Chloro-phenyl)-3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 37896-09-6 2-(3-chloro-phenyl)-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 108474-71-1 2-(2-amino-4-chloro-benzoyl)-benzoic acid 

Relevant articles and documents

Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions

A series of N-substituted phthalimides was synthesized by a thermal reaction between N,N0-disubstituted ureas and phthalic acid catalyzed by imidazole in solventless conditions. The products have been obtained in moderate to good yields (53-92%). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

A phthalimidation protocol that follows protein defined parameters

This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.