2550-73-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 26, 1959 DOI: 10.1021/jo01083a008

InChI:InChI=1/C10H4N2O4/c13-7-3-1-4-6(10(16)12-8(4)14)2-5(3)9(15)11-7/h1-2H,(H,11,13,15)(H,12,14,16)

Upstream product

• 247045-28-9 4,5-dibromophthalimide 
• 544-92-3 copper(I) cyanide 
• 76660-17-8 pyromellitic diimide.formamide 
• 27086-32-4 2,5-diformyl-terephthalic acid 
• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 
• 6183-35-3 1,2,4,5-Benzenetetracarboxylic acid tetraamide 
• 89-32-7 Pyromellitic dianhydride 
• 13731-82-3 2,5-dibromoterephtalic acid 

Downstream Products

• 945-30-2 2,5-diaminoterephthalic acid 
• 23565-55-1 N,N/-bis-hydroxymethylpyromellitic diimide 
• 760951-07-3 2-(5-{4-[bis-(4-tert-butyl-phenyl)-(4-isopropyl-phenyl)-methyl]-phenoxy}-pentyl)-6-(5-hydroxy-pentyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 77762-96-0 2,6-Bis-(4-pyrrolidin-1-yl-but-2-ynyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 77762-97-1 2,6-Bis-(4-piperidin-1-yl-but-2-ynyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 77763-00-9 2,6-Bis-[4-(2-methyl-piperidin-1-yl)-but-2-ynyl]-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 77762-98-2 2,6-Bis-(4-azepan-1-yl-but-2-ynyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 77763-01-0 2,6-Bis-[4-((2S,6R)-2,6-dimethyl-piperidin-1-yl)-but-2-ynyl]-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 1361950-38-0 C₃H₇NO*C₉H₇Cl₂N₅*C₁₀H₄N₂O₄ 
• 23328-66-7 bis-N-glycidylpyromellitic diimide 
• 712-74-3 1,2,4,5-tetracyanobenzene 
• 6183-35-3 1,2,4,5-Benzenetetracarboxylic acid tetraamide 
• 32338-53-7 2,5-dicarbamoyl-terephthalic acid 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Screening of Novel Azetidin-2-ones Derived from Pyromellitic Diimide via [2+2]-Cycloaddition Reaction

A series of novel 2-azetidinone derivatives have been obtained starting from pyromellitic dianhydride. Pyromellitic dianhydride was converted to pyromellitic diimide using sodium cyanate, and the diimide was alkylated with ethyl chloroacetate. The resulting diester was treated with hydrazine hydrate to obtain dihydrazide which reacted with substituted pyridine-2-carbaldehydes to give the corresponding Schiff bases, and [2+2]-cycloaddition of the latter with chloroacetyl chloride in the presence of triethylamine afforded the target azetidin-2-one derivatives. The newly synthesized compounds showed high antimicrobial activities against some bacterial and fungal strains.

Precursors for pyromellit-bridged silica sol-gel hybrid materials

Bridged bis(trialkoxysilylalkyl)pyromellitic diimides 3-6 were prepared as single-source precursors for sol-gel derived organic-inorganic hybrid materials. The synthesis route starts with the formation pyromellit diimide 1 from pyromellitic dianhydride and hexamethyldisilazane (HMDS), followed by metallation of the NH groups to give the dipotassium salt 2. The four molecular hybrid precursors 3-6 were obtained according to the first step of the Gabriel synthesis. The reaction rates were studied as a function of the alkyl chain length and the nature of the halide (Cl vs. I). All products 1-6 were comprehensively analysed using FT-IR, 1H and 13C NMR spectroscopy as well as elemental analysis, and - in the case of 3-6 - also with 29Si NMR spectroscopy. For compounds 3 (with propylene groups and methoxy substituents) and 6 (with methylene groups and ethoxy substituents) single crystal X-ray structures were determined and discussed. Hydrolysis and condensation of the alkoxides 3-6 were carefully monitored with solution 29Si and 1H NMR spectroscopy providing a basis for further studies on the formation of silica-pyromellit organic-inorganic hybrids from precursors 3-6. Finally the formation of flexible and transparent hydride films using precursors 4 and 6 was proved.

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.

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.

Phthalimide end capping monomer and its preparation method and application

The invention relates to a phthalimide-terminated monomer, which has a structural general formula as following: in a H-R4-H formula, R4 is one in the specification, R3 in the specification is one of O, S, SO2, CO, C(CH3)2, C(CF3)2. The invention also provides a preparation method of the phthalimide-terminated monomer and an application of the phthalimide-terminated monomer in preparation of phthalonitrile resin.

An expedient and convenient approach for one-pot synthesis of 1H-isoindole-1,3(2H)-diones

An easy and expedient method for the one-pot synthesis of 1H-isoindole-1,3(2H)-diones has been developed by the reaction of the corresponding cyclic anhydrides with guanidinium chloride as a nitrogen source in the presence of FeCl3 as a catalyst under mild reaction conditions.

Synthesis of some new heterocyclic nitrogen compounds starting from pyromellitic dianhydride

Pyromellitic dianhydride 1 was used as starting compound for the synthesis of some new derivatives of condensed dipyrrole, dibenzoxazine, and dipyridazine. Thus, the diimide 2 was formed on fusion of 1 with urea, thiourea and/or thiosemicarbazide. Also, 1 reacted with benzylamine to give terephthalic acid derivative 3 which on fusion afforded the cyclic diimide 4. The reaction of 1 with o-aminothiophenol under different reaction conditions was investigated to give 5 in acetic acid or 6 in toluene and the later could be decarboxylated to 7. On the other hand, the action of AlCl3 on 1 in presence of reactive aromatic substrates afforded the corresponding isomers 8a-d and 9a-d. which could be cyclized using hydroxylamine hydrochloride to give the dioxazine isomers 10a-d and 11a-d. The dioxazine isomers 10b and 11b were also obtained when 14 was allowed to react with AlCl3 in anisol. Cyclization of 8a-d and/or 9a-d using hydrazine or phenylhydrazine gives the dipyridazine isomers 13a-h and/or 14a-f respectively.

Formamide, a novel challenging reagent for the direct synthesis of non-N-substituted cyclic imides

Aliphatic and aromatic cyclic imides have been prepared in high to moderate yields from cyclic carboxylic anhydrides or corresponding dicarboxylic acids, using formamide as reagent at 170-180°C for 5-6 hours. In the case of aromatic products with lower solubility in formamide, we used N-methyl-2-pyrrolidinone (NMP) as supplementary solvent, which facilitates the reaction.

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.

Imidation of cyclic carboxylic anhydrides under microwave irradiation

Efficient and facile conversion of cyclic carboxylic anhydrides to corresponding imides with formamide under microwave irradiation is described.