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Usage

Uses

Used in Pharmaceutical Synthesis:
4,5-Dichlorophthalimide is used as a reactant in the synthesis of various pharmaceutical compounds, such as 5′-N-(4′′,5′′-dichlorophthaloyl)-3′-azido-2′,3′-dideoxythymidine and 2-amino-4,5-dichlorobenzoic acid. It plays a crucial role in the development of new drugs and therapies.
Used in Chemical Research:
4,5-Dichlorophthalimide serves as a reactant in the synthesis of 4,5-dichloro-1,2-benzenedicarboxamide, contributing to the advancement of chemical research and the discovery of new compounds with potential applications.
Used in Catalyst Development:
In the field of catalysis, 4,5-dichlorophthalimide is used as an additive in the Ir-BICP catalyzed asymmetric hydrogenation of 2,3,3-trimethylindolenine to improve enantioselectivity, enhancing the efficiency and selectivity of chemical reactions.
Used in Material Science:
4,5-Dichlorophthalimide is utilized as a reactant in the synthesis of octachloro-Cu-phthalocyanine, a compound with potential applications in material science, such as in the development of new materials with specific properties.
Used in Organic Chemistry:
As a reagent, 4,5-dichlorophthalimide is employed in the synthesis of 7-tert-butylthianthrene-2,3-dicarboxylic imide, contributing to the expansion of organic chemistry and the creation of new organic compounds.
Used in Synthesis of N-(3-bromopropyl)-4,5-dichlorophthalimide:
4,5-Dichlorophthalimide serves as a starting material in the synthesis of N-(3-bromopropyl)-4,5-dichlorophthalimide, which can be used in various chemical applications and reactions.
Used in Phosphine-Catalyzed Allylic Substitution:
4,5-Dichlorophthalimide acts as a nucleophilic partner in the phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates to form N-protected β-amino phosphonic acid esters, a reaction with potential applications in the synthesis of complex organic molecules.

InChI:InChI=1/C8H3Cl2NO2/c9-5-1-3-4(2-6(5)10)8(13)11-7(3)12/h1-2H,(H,11,12,13)

Upstream product

• 942-06-3 4,5-dichlorophthalic anhydride 
• 106727-86-0 4,5-dichlorophthalic acid dimethyl ester 
• 56962-08-4 4,5-dichlorophthalic acid 
• 110568-92-8 2-carbamoyl-4,5-dichlorobenzoic acid 

Downstream Products

• 147699-62-5 4,5-dichloro-1,2-benzenedicarboxamide 
• 3682-31-3 6,7-dichloro-2,3-dihydrophthalazine-1,4-dione 
• 865537-16-2 N-triisopropylsilyl-4,5-bis-(4-methoxyanilino)phthalimide 
• 865537-18-4 N-triisopropylsilyl-4,5-bis-(4-nitroanilino)phthalimide 
• 145915-63-5 4,5-bis-(4-methoxyanilino)phthalimide 
• 139152-08-2 4,5-dichlorophthalonitrile 
• 147699-69-2 4,5-bis(propylthio)benzene-1,2-dinitrile 
• 147699-63-6 1,2-diisocyano-3,4-diphenoxy benzene 
• 147699-67-0 4,5-bis(phenylthio)-1,2-dicyanobenzene 
• 147699-68-1 4,5-bis(pyridin-3-yloxy)phthalonitrile 
• 147699-65-8 4,5-bis-(4-hydroxyphenoxy)phthalonitrile 

Relevant academic research and scientific papers

ADAMTS INHIBITORS, PREPARATION METHODS AND MEDICINAL USES THEREOF

Compounds of formula (I) useful as inhibitors of ADAMTS-5 and/or ADAMTS-4, pharmaceutical compositions thereof, and use of them as therapeutic agents for the treatment of diseases involving degradation of cartilage or disruption of cartilage homeostasis, in particular osteoarthrosis and/or rheumatoid arthritis, are disclosed.

Surface modified polymer hollow nanocapsules, and method for preparing the same

The present invention relates to surface-modified polymer hollow nanocapsules in which polymer hollow nanocapsules, formed via polymerization of a composition containing a compound represented by chemical formula 1, are surface-modified to have a positive zeta potential when dispersed in water; and a method of preparing the same. In the chemical formula 1: X is subphthalocyanine, phthalocyanine, or porphyrin; L_1 is -OR_1- or -SR_2-, wherein the R_1 and R_2 are each independently a direct bond, an alkylene group having 1-10 carbon atoms, an alkenylene group having 2-10 carbon atoms, a cycloalkylene group having 6-20 carbon atoms, a cycloalkenylene group having 6-20 carbon atoms, or an arylene group having 6-20 carbon atoms; Y_1 is a vinyl group, an acryl group, a methacryl group, a thiol group, or an amine group; and m is an integer of 3-10.COPYRIGHT KIPO 2018

Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions

Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.

A Multifunctional Subphthalocyanine Nanosphere for Targeting, Labeling, and Killing of Antibiotic-Resistant Bacteria

Developing a material that can combat antibiotic-resistant bacteria, a major global health threat, is an urgent requirement. To tackle this challenge, we synthesized a multifunctional subphthalocyanine (SubPc) polymer nanosphere that has the ability to target, label, and photoinactivate antibiotic-resistant bacteria in a single treatment with more than 99 % efficiency, even with a dose as low as 4.2 J cm-2 and a loading concentration of 10 nM. The positively charged nanosphere shell composed of covalently linked SubPc units can increase the local concentration of photosensitizers at therapeutic sites. The nanosphere shows superior performance compared to corresponding monomers presumably because of their enhanced water dispersibility, higher efficiency of singlet-oxygen generation, and phototoxicity. In addition, this material is useful in fluorescence labeling of living cells and shows promise in photoacoustic imaging of bacteria in vivo.

Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase

Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references.

A facile reprecipitation method for the preparation of polyimide hollow spheres with controllable morphologies and permeable shell

We present our preliminary work on the fabrication of polyimide hollow sphere by reprecipitation. Through fine-tuning the PAA concentration, many intriguing shapes, including deflated capsules, bowl-shaped and dimple-like hollow spheres can be obtained. Adding salt to the PAA solution helps the formation of PI hollow spheres with complete shells. The morphologies can be fixed through imidization, thus obtaining a controllable and reproducible method to prepare high-performance polyimide hollow spheres with various morphologies.

Rapid and convenient microwave-assisted synthesis of aromatic imides and N-hydroxymethylimides

Extremely simple high-yielding and rapid microwave-assisted synthesis of wide array of aromatic mono and diimides and mono- and bis-N-hydroxymethylimides is reported.

Analogues of N(α)-(4-amino-4-deoxypteroyl)-N(δ)-hemiphthaloyl-L- ornithine (PT523) modified in the side chain: Synthesis and biological evaluation

Four heretofore undescribed side chain analogues of N(α)-(4-amino-4- deoxypteroyl)-N(δ)-hemiphthaloyl-L-ornithine (PT523, 4) were synthesized via straightforward methods of antifolate chemistry, and their properties were compared with those of PT523 and two related compounds with the aim of defining the contribution of the hemiphthaloyl-L-ornithine moiety to the exceptional in vitro antitumor activity of this novel non-polyglutamatable aminopterin analogue. The IC50 values of N(α)-(4-amino-4-deoxypteroyl)- N(β)-hemiphthaloyl-L-2,3-diaminopropanoic acid (10) and N(α)-(4-amino-4- deoxypteroyl)-N(γ)-hemiphthaloyl-L-2,4-diaminobutanoic acid (9) against A549 human non-small-cell lung carcinoma cells in culture were 23 and 22 nM, whereas those of PT523 and N(α)-(4-amino-4-deoxypteroyl)-N(ε)- hemiphthaloyl-L-lysine (8) were 1.3 and 5.2 nM. A decrease in the in vitro activities of 8 and 9 relative to PT523 was also observed against the panel of cell lines used by the National Cancer Institute to screen new drugs. However the potency of 8 and 9 remained several times greater than that of the historical control methotrexate against many of the cell lines in the screening panel. In an in vivo tumor model, SCC-VII murine squamous cell carcinoma, 9 and methotrexate were well tolerated as 5-day continuous infusions at doses of 0.52 and 0.75 mg/kg/day, whereas the highest tolerated dose of PT523 on this schedule was 0.19 mg/kg/day, in agreement with its lower IC50 in culture. To assess the importance of the hemiphthaloyl group in PT523, N(α)-(4-amino-4-deoxypteroyl)-N(δ)-isophthaloyl-L-ornithine (11), N(α)-(4-amino-4-deoxypteroyl)-N(δ)-terephthaloyl-L-ornithine (12), and N(α)-(4-amino-4-deoxypteroyl)-N(δ)-(4,5-dichlorohemiphthaloyl)-L-ornithine (13) were also synthesized. The IC50 values of 11 and 12 against A549 cells were 45 and 3300 nM, as compared with 1.3 nM for PT523 and 23 nM for methotrexate. In a clonogenic assay against SCC25 human squamous cell carcinoma cells, the IC50 values of 11 and 12 were 2.9 and 72 nM, as compared with 0.3 nM for PT523 and 27 nM for methotrexate. Thus, activity was decreased by moving the aromatic carboxyl group in PT523 to the meta position and was further diminished by moving it to the para position. The IC50 of the halogenated analogue 13 against SCC25 human head and neck squamous carcinoma cells was 18 nM, suggesting lack of tolerance for this 4,5- disubstitution in the phthaloyl moiety. Our results suggest that the combination of a hemiphthaloyl group and three CH2 groups in the side chain are critical determinants of the potent in vitro activity of PT523.

A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines

4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propylthio)-1,2-dicyanobenzenes 6 which were converted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in high yields to octasubstituted phthalocyanines (tetrabenzoporphyrazines) 7. Some compounds 7 contain eight free phenolic, carboxylic acid or pyridyl groups.