40314-06-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylphthalimide 99 is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and improve existing ones.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Methylphthalimide 99 serves as a building block, facilitating the creation of complex organic molecules and contributing to advancements in chemical research and development.
Used in Dye and Pigment Production:
4-Methylphthalimide 99 is utilized in the production of dyes and pigments, where its chemical properties enhance the colorfastness and stability of these products, making them suitable for various applications in industries such as textiles, plastics, and printing inks.
Used in Industrial Chemicals:
4-METHYLPHTHALIMIDE 99 is also employed in the manufacturing of other industrial chemicals, leveraging its reactivity and stability to improve the performance and quality of the final products in various industrial applications.

InChI:InChI=1/C9H7NO2/c1-5-2-3-6-7(4-5)9(12)10-8(6)11/h2-4H,1H3,(H,10,11,12)

Upstream product

• 4316-23-8 4-methylphthalic acid 
• 19438-61-0 4-methylphthalic anhydride 
• 3317-61-1 5,5-Dimethyl-1-pyrroline N-oxide 
• 63089-50-9 4-methylphthalonitrile 
• 1608-47-5 4-Methyl-1,2-diiodobenzene 
• 77287-34-4 formamide 
• 874-60-2 4-methyl-benzoyl chloride 
• 33757-49-2 4-methyl-N-(quinolin-8-yl)benzamide 
• 4593-38-8 5-methylindan-1-one 
• 24623-20-9 2,3-dihydro-6-methyl-1H-inden-1-one 
• 1711-06-4 3-Methylbenzoyl chloride 
• 99-04-7 m-Toluic acid 
• 52107-96-7 2-iodo-5-methylbenzoyl chloride 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 

Downstream Products

• 63089-47-4 4-methyl-phthalic acid diamide 
• 1153421-34-1 methyl 2-((methoxycarbonyl)amino)-5-methylbenzoate 
• 1356116-12-5 methyl 2-((methoxycarbonyl)amino)-4-methylbenzoate 
• 1438436-39-5 C₁₉H₁₉NO₂ 
• 1438436-40-8 C₁₉H₁₉NO₂ 
• 119596-20-2 2-(4-isopropylphenyl)-5-methylisoindoline-1,3-dione 
• 1606159-93-6 2-(cyclohex-2-en-1-yl)-5-methylisoindoline-1,3-dione 
• 40314-04-3 2-cyclohexyl-5-methylisoindoline-1,3-dione 
• 2133-65-5 N-cyclohexylphthalimide 

Relevant academic research and scientific papers

Ni-Catalyzed Direct Carboxylation of Aryl C?H Bonds in Benzamides with CO2

The direct carboxylation of inert aryl C?H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C?H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)?Ni(II)?Ni(I) catalytic cycle may be involved in this reaction. (Figure presented.).

Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea

N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.

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.

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

Synthesis method of phthalimide and phenyl ring-substituted phthalimide derivative

The invention provides a synthesis method of phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method comprises that aromatic ketone and ammonia gas or an ammonia gas precursor as substrates and air or oxygen as an oxygen source undergo a reaction under catalyst action and liquid phase conditions to produce phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method is mild, realizes high oxidation efficiency and a high product yield, utilizes oxygen or air as an oxygen source, is economic and eco-friendly and has a good application prospect.

Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides

A method for direct carbonylation of aminoquinoline benzamides has been developed. Reactions proceed at room temperature in trifluoroethanol solvent, use oxygen from air as an oxidant, and require Mn(OAc)3 as a cocatalyst. Benzoic and acrylic a

MATRIX METALLOPROTEINASE INHIBITORS

The present invention relates to methyl sulfonamides and N-formamides derivatives of formula (I) and to processes for their syntheses. The invention also relates to pharmacological compositions containing these derivatives and methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatie arthritis, psoriasis, pulmonary fibrosis, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, dry eye, neointimal proliferation which leads to restenosis and ischemic heart failure, stroke, renal disease, tumor metastasis, and other inflammatory disorders characterized by over expression and over activation of an matrix metalloproteinase using the compounds.

Carbon monoxide-free one-step synthesis of isoindole-1,3-diones by cycloaminocarbonylation of o-haloarenes using formamides

A new carbon monoxide-free, solvent-free, single step protocol for the synthesis of isoindole-1,3-diones from o-haloarenes using palladium acetate and xantphos catalysis is reported. The wider applicability of this protocol for several types of o-iodoarenes and a few o-bromoarenes makes it attractive. Aryl iodides and aryl bromides provided moderate to excellent yields of up to 93 %.

Metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles: Syntheses of oxadiazolines as well as phthalamide-PdII and dihydropyrrolyl-iminoisoindolinone-Pd II complexes with high catalytic activity in suzuki-miyaura cross-coupling reactions

The previously unknown reactions between phthalonitriles, 1,2-(CN) 2(C6)R1R2R3R4 1 (1a, R1 = R2 = R3 = R4 = H; 1b, R1 = R2 = R4 = H, R3 = CH 3; 1e, R1 = R4 = H, R2 = R 3 = Cl; 1d, R1 = R2 = R3 = R 4 = Cl; 1e, R1 = R2 = R3 = R 4 = F), and a cyclic nitrone, -O+ N=CHCH 2CH2CMe2 2, proceed under heating in a sealed tube to give phthalimides 3, 2-oxadiazolyl-benzonitriles 4 or ortho-bis(oxadiazolyl)tetrafluorobenzene 4e′. In the presence of palladium(II) chloride, phthalonitriles 1 react with 2 at room temperature, to give bis(pyrrolidin-2-ylidene)phthalamide PdII complexes 5 via metal-promoted rupture of the N-O bond of the oxadiazoline ring. The ketoimine ligands thus generated can be liberated from the metal by displacement with a diphosphine. Although the first [2+3] cycloaddition of 2 to 1 can occur in the absence of the metal to give the monocycloadducts 4, the second [2+3] coupling at the still-unreacted cyano group requires its activation by coordination to Pdc, affording complexes 6 containing two ligated oxadiazolyl-benzonitriles. These ligands undergo either i) further cycloaddition with 2 to afford ultimately (upon rearrangement) the bis(pyrrolidinylidene)phthalamide complexes 5 or ii) N-O bond cleavage in the oxadiazoline ring with intramolecular attack of the imine nitrogen on the cyano carbon and bridging to a second Pd II center to afford dimeric palladium(II) complexes 7, with chloride bridges, that bear a dihydropyrrolyl-iminoisoindolinone, a new type of ligand. The compounds were characterized by IR, 1H, and 13C NMR spectroscopy, ESI MS or FAB+ MS, elemental analyses and, in the case of 4c, 5 a, 5c, and 7c, also by X-ray diffraction analysis. Complexes 5a and 7c show high catalytic activity for the Suzuki-Miyaura cross-coupling reaction of bromobenzene and phenylboronic acid and give biphenyl in high yields with turnover frequencies (TOFs) of up to 9.0 × 105 h-1.