65833-01-4

Basic information

• Product Name: 1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE
• Synonyms: 1-(4-IODO-PHENYL)-PYRROLE-2,5-DIONE;1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE;ASISCHEM D51115;N-(4-IODOPHENYL)MALEIMIDE;TIMTEC-BB SBB002109;1-(4-Iodophenyl)-1H-pyrrole-2,5-dione, 2,5-Dioxo-1-(4-iodophenyl)-1H-pyrrole;NSC 88871
• CAS NO: 65833-01-4
• Molecular Formula: C₁₀H₆INO₂
• Molecular Weight: 299.06
• Mol File: 65833-01-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 160
• Boiling Point: 384.8 °C at 760 mmHg
• Flash Point: 186.5 °C
• Appearance: /
• Density: 1.963 g/cm³
• Vapor Pressure: 3.99E-06mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: 1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE(65833-01-4)
• EPA Substance Registry System: 1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE(65833-01-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 65833-01-4(Hazardous Substances Data)

Usage

General Description

1-(4-iodophenyl)-1H-pyrrole-2,5-dione, also known as iodophenylpyrroledione, is a chemical compound with the molecular formula C10H6INO2. It is a pyrrole-2,5-dione derivative with a substituted iodophenyl group attached to the 1-position. 1-(4-IODOPHENYL)-1H-PYRROLE-2,5-DIONE is commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. It exhibits potential biological activities and has been studied for its anti-inflammatory, antioxidant, and antimicrobial properties. Additionally, it has potential applications in material science and organic electronics due to its unique electronic and optical properties.

InChI:InChI=1/C10H6INO2/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(12)14/h1-6H

Upstream product

• 108-31-6 maleic anhydride 
• 540-37-4 p-aminoiodobenzene 
• 17280-49-8 (Z)-3-(4-Iodo-phenylcarbamoyl)-acrylic acid 
• 200706-68-9 C₁₀H₈INO₃ 
• 92636-36-7 1-(4-iodophenyl)pyrrole 

Downstream Products

• 134220-55-6 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-iodo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-iodo-phenyl)-4a-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-48-7 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-iodo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-iodo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 1312323-95-7 3-{2-[(1-ethylpropylidene)hydrazono]-1-methylbutyl}-1-(4-iodophenyl)pyrrolidine-2,5-dione 
• 1312324-03-0 3-[2-(cyclopentylidenehydrazono)cyclopentyl]-1-(4-iodophenyl)pyrrolidine-2,5-dione 
• 1312324-11-0 2-(3,4,4a,5,6,7-hexahydro-3-oxo-2H-cyclopenta[c]pyridazin-4-yl)-N-(4-iodophenyl)acetamide 
• 1312324-07-4 3-[2-(cyclohexylidenehydrazono)cyclohexyl]-1-(4-iodophenyl)pyrrolidine-2,5-dione 
• 1312324-15-4 2-(2,3,4,4a,5,6,7,8-octahydro-3-oxocinnolin-4-yl)-N-(4-iodophenyl)acetamide 
• 723742-85-6 2-(2,3,4,5-tetrahydro-6-methyl-3-oxopyridazin-4-yl)-N-(4-iodophenyl)acetamide 
• 1567324-45-1 (3aR,6aS)(Z/E)-2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]-dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-5-(4-iodophenyl)-dihydro-4H-[1,3]dithiolo[4,5-c]pyrrole-4,6(5H)-dione 
• 1567324-54-2 (3aR,6aS)(Z/E)-2-(4-benzyl-3-oxo-6-thioxo-3H,4H-[1,2]-dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-5-(4-iodophenyl)-dihydro-4H-[1,3]dithiolo[4,5-c]pyrrole-4,6(5H)-dione 
• 1567324-57-5 (2Z/E,2′E/Z,3aR,3a′R,6aS,6a′S)-2,2′-(4-ethyl-2,6-dithioxothiomorpholine-3,5-diylidene)bis(5-(4-iodophenyl)dihydro-4H-[1,3]dithiolo[4,5-c]pyrrole-4,6(5H)-dione) 

Relevant articles and documents

Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.

Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite

A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cycloadditions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N′-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.