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

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 
• 346695-24-7 toluene-4-sulfonic acid-(2-chloro-5-nitro-anilide) 
• 857005-56-2 toluene-4-sulfonic acid-(2-chloro-N-methyl-5-nitro-anilide) 
• 37896-13-2 2-(2-chlorophenyl)-3-hydroxyisoindolin-1-one 
• 1020-39-9 N-(2-chlorophenyI)benzamide 

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.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

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.