2314-76-3

Usage

Uses

Used in Dye and Pigment Production:
N-M-TOLYLPHTHALIMIDE is used as a chemical intermediate for the synthesis of various dyes and pigments, contributing to the coloration and stability of these products in different applications.
Used in the Rubber Industry:
N-M-TOLYLPHTHALIMIDE is used as a vulcanization accelerator, improving the elasticity, strength, and durability of rubber products, thereby enhancing their performance and longevity.
Used in Pharmaceutical and Agrochemical Synthesis:
N-M-TOLYLPHTHALIMIDE is utilized as a key component in the production of pharmaceuticals and agrochemicals, playing a crucial role in the development of new and effective compounds for medical and agricultural use.

InChI:InChI=1/C15H11NO2/c1-10-5-4-6-11(9-10)16-14(17)12-7-2-3-8-13(12)15(16)18/h2-9H,1H3

Upstream product

• 85-44-9 phthalic anhydride 
• 108-44-1 1-amino-3-methylbenzene 
• 85-72-3 N-meta-tolyl phthalamic acid 
• 73357-42-3 2-(3-methylphenyl)-2,3-dihydro-1H-isoindole 
• 670-54-2 ethenetetracarbonitrile 
• 136918-14-4 phthalimide 
• 17933-03-8 m-tolylboronic acid 
• 178933-91-0 [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetic acid 
• 108-88-3 toluene 
• 524-38-9 N-hydroxyphthalimide 
• 5672-90-2 N-(trifluoromethyl)acyloxyphthalimide 
• 3481-09-2 N-chlorophthalimide 
• 83-33-0 inden-1-one 
• 64-18-6 formic acid 

Downstream Products

• 85-72-3 N-meta-tolyl phthalamic acid 
• 314-81-8 2-[3-(trifluoromethyl)phenyl]-1H-isoindole-1,3(2H)-dione 
• 129747-78-0 N-(3-Bromomethylphenyl)phthalimide 
• 205759-45-1 3-N-phthalimidobenzaldehyde 
• 1532556-62-9 3-ethyl-3-hydroxy-2-(m-tolyl)isoindolin-1-one 

Relevant academic research and scientific papers

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature

The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.

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.

PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides

A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.

Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion

A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.

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.

A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes

In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.

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.

H-β-zeolite catalyzed transamidation of carboxamides, phthalimide, formamides and thioamides with amines under neat conditions

Efficient transamidation of unactivated carboxamides, phthalimides, formamides and thioamides with amines under solvent-free conditions using H-β-zeolite as a green and recyclable heterogeneous catalyst is described. Easy work up, high purity of the products, recyclability and environmentally-friendly nature of the catalyst are the attractive features of the present methodology. This is the first report for the transamidation of thioamides under heterogeneous conditions.

N -aminopyridinium salts as precursors for N-centered radicals - Direct amidation of arenes and heteroarenes

Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.

Regioselective gold-catalyzed oxidative C-N bond formation

A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.