22698-95-9

Basic information

• Product Name: n-(2-chlorophenyl)phthalimide
• Synonyms: 2-(2-Chlorophenyl)-2H-isoindole-1,3-dione;N-(o-Chlorophenyl)phthalimide
• CAS NO: 22698-95-9
• Molecular Formula: C₁₄H₈ClNO₂
• Molecular Weight: 257.67
• Mol File: 22698-95-9.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 414.9°Cat760mmHg
• Flash Point: 204.7°C
• Appearance: /
• Density: 1.441g/cm³
• Vapor Pressure: 4.29E-07mmHg at 25°C
• Refractive Index: 1.672
• CAS DataBase Reference: n-(2-chlorophenyl)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: n-(2-chlorophenyl)phthalimide(22698-95-9)
• EPA Substance Registry System: n-(2-chlorophenyl)phthalimide(22698-95-9)

Safety Data

• Hazardous Substances Data: 22698-95-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H8ClNO2/c15-11-7-3-4-8-12(11)16-13(17)9-5-1-2-6-10(9)14(16)18/h1-8H

Upstream product

• 85-44-9 phthalic anhydride 
• 95-51-2 o-chloroaniline 
• 136918-14-4 phthalimide 
• 108-90-7 chlorobenzene 
• 3481-09-2 N-chlorophthalimide 
• 83-33-0 inden-1-one 
• 6273-12-7 N-(2-chloro-phenyl)-phthalamic acid 
• 73357-41-2 2-(2-Chlorphenyl)-isoindolin 
• 670-54-2 ethenetetracarbonitrile 

Downstream Products

• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 85-51-8 2-amino-3-chlorobenzophenone-2'-carboxylic acid 
• 79419-88-8 2-(2-Chloro-phenyl)-3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 79419-93-5 2-(2-Chloro-phenyl)-3-(3-chloro-phenyl)-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 37896-13-2 2-(2-chlorophenyl)-3-hydroxyisoindolin-1-one 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 857005-56-2 toluene-4-sulfonic acid-(2-chloro-N-methyl-5-nitro-anilide) 
• 346695-24-7 toluene-4-sulfonic acid-(2-chloro-5-nitro-anilide) 

Relevant articles and documents

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.

Synthetic method for N-substituted imide

The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.

Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines

Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.