85342-65-0

Usage

Uses

Used in Scientific Research:
4,5,6,7-tetrachloro-2-hydroxy-1H-isoindole-1,3(2H)-dione is used as a research compound for [application reason]. Due to its complex structure and the presence of multiple chloro atoms, it may be employed in studies related to organic chemistry, chemical synthesis, or material science.
Used in Industrial Applications:
4,5,6,7-tetrachloro-2-hydroxy-1H-isoindole-1,3(2H)-dione is used as a chemical intermediate for [application reason]. Its potential applications in the industry could be in the development of new materials, dyes, or pharmaceuticals, although further research is needed to confirm its specific uses.
Used in Pharmaceutical Development:
4,5,6,7-tetrachloro-2-hydroxy-1H-isoindole-1,3(2H)-dione is used as a potential drug candidate for [application reason]. Its unique chemical properties may offer opportunities for the development of new therapeutic agents, but more research is required to understand its pharmacological profile and potential toxicological effects.
Note: The specific application reasons and industries are not provided in the materials, so they are left as placeholders to be filled in with accurate information once it becomes available.

Upstream product

• 117-08-8 tetrachlorophthalic anhydride 
• 1571-13-7 3,4,5,6-tetrachlorophthalimide 

Relevant academic research and scientific papers

Petroleum-dispersing and antimicrobial activity of newly synthesized polymeric surfactants tethering tetrachlorophthalimide moiety

The development of compounds with dual or multi-functions or activities is being paid attention in the scientific community. Herein, two series of phthalimide-containing copolymers were synthesized and structurally characterized and their potency against selected microbial strains was evaluated. Our study mainly focused on evaluating both the antimicrobial and surface activities of new corresponding polymeric cationic surfactants for removing petroleum thin films with their increased dispersing capacity. The synthesis process includes the formation of N-methacryloyloxytetrachlorophthalimide monomer, homopolymerization, and exchange reactions with various amino- and hydroxy-compounds for the synthesis of copolymers. Lastly, polymeric surfactants were obtained via the quaternization of some copolymers with dimethyl sulfate. Among the tested derivatives, compounds 5a, 5b, 6c, 6d, and 7b showed higher activities than the standard drugs which reached 2.45-fold (44?mm against A. niger) in copolymer 5b. Besides, the three polymeric surfactants displayed strong surface activity features including Krafft point, foaming, and emulsifying power. Moreover, polymeric surfactant 7b exhibited strong dispersion behavior for petroleum in both undiluted form (Kd from 91.60 to 93.20%, τ = 30–96?h) and diluted form (Kd from 95.7 to 98.1%, τ = 5–96?h).

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation

A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk- 2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.

Photochemical Organocatalytic Benzylation of Allylic C–H Bonds

We report a radical-based organocatalytic method for the direct benzylation of allylic C–H bonds. The process uses nonfunctionalized allylic substrates and readily available benzyl radical precursors and is driven by visible light. Crucial was the identification of a dithiophosphoric acid that performs two distinct catalytic roles, sequentially acting as a catalytic donor for the formation of photoactive electron donor–acceptor (EDA) complexes and then as a hydrogen atom abstractor. By mastering these orthogonal radical generation paths, the organic catalyst enables the formation of benzylic and allylic radicals, respectively, to then govern their selective coupling. The protocol was also used to design a three-component radical process, which increased the synthetic potential of the chemistry.

Preparation method of free radical initiator and application of free radical initiator in oxidation reaction

The invention discloses a preparation method of a free radical initiator, the preparation method comprises the following steps: feeding a hydroxylamine raw material, inorganic base and water according to a ratio, and carrying out acid-base neutralization reaction at 0-25 DEG C to dissociate hydroxylamine; adding tetrachlorophthalic anhydride, stirring at room temperature to react for 0.5-2 hours, reacting at 60-95 DEG C for 4-12 hours, washing with water, and drying at 60-80 DEG C for 10-24 hours to obtain an N-hydroxyl tetrachlorophthalimide crude product; and recrystallizing the N-hydroxyl tetrachlorophthalimide crude product in a mixed solvent of toluene and ethanol, filtering, and drying at 60-80 DEG C to obtain the N-hydroxyl tetrachlorophthalimide free radical initiator. According to the method, the adopted raw materials are simple, the conditions are easy to control, the preparation technology is green and environmentally friendly, the preparation repeatability is good, the free radical initiator is used in the oxidation reaction, a high-purity and high-yield product can be obtained, and the product obtained after repeated use still has high separation yield and purity.

Kinetics of N-oxyl Radicals' Decay

N-oxyl radicals of various structures were generated by oxidation of corresponding N-hydroxy compounds with iodobenzene diacetate, [bis(trifluoroacetoxy)]iodobenzene, and ammonium cerium(IV) nitrate in acetonitrile. The decay rate of N-oxyl radicals follows first-order kinetics and depends on the structure of N-oxyl radicals, reaction conditions, and the nature of the solvent and oxidant. The values of the self-decay constants change within 1.4 × 10-4 s-1 for the 3,4,5,6-tetraphenylphthalimide-N-oxyl radical to 1.4 × 10-2 s-1 for the 1-benzotriazole-N-oxyl radical. It was shown that the rate constants of the phthalimide-N-oxyl radicalsê? self-decay with different electron-withdrawing or-donor substituents in the benzene ring are higher than that of the unsubstituted phthalimide-N-oxyl radical in most cases. The solvent effect on the process of phthalimide-N-oxyl radical self-decomposition was investigated. The dependence of the rate constants on the Gutmann donor numbers was shown.

Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex

The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp3)-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.

Microwave-assisted synthesis of N-hydroxyphthalimide derivatives

N-Hydroxyphthalimide derivatives are readily obtained in good yields by the reaction of phthalic anhydrides with hydroxylamine hydrochloride in the presence of pyridine under microwave irradiation.

Mild and convenient one pot synthesis of N-hydroxyimides from N-unsubstituted imides

A new, one pot synthesis of various N-hydroxyimides from N-unsubstituted imides is described. Imides are first transformed into their N-Boc derivatives, which are next reacted with aqueous hydroxylamine, providing crystalline hydroxylammonium salts of the corresponding N-hydroxyimides. Filtration and acidic workup affords pure N-hydroxyimides.