4338-06-1

Basic information

• Product Name: N-(4-NITROPHENYL)MALEIMIDE
• Synonyms: 1-(4-nitrophenyl)-3-pyrroline-2,5-quinone;N-(4-Nitrophenyl)maleimide;Maleimide, N-(p-nitrophenyl)-;ART-CHEM-BB B001449;ASISCHEM S97819;AURORA KA-3853;AKOS B001449;AKOS MSC-0023
• CAS NO: 4338-06-1
• Molecular Formula: C₁₀H₆N₂O₄
• Molecular Weight: 218.17
• Product Categories: N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides
• Mol File: 4338-06-1.mol
• Article Data: 44

Chemical Properties

• Melting Point: 170°C
• Boiling Point: 418.5 °C at 760 mmHg
• Flash Point: 206.9 °C
• Appearance: /
• Density: 1.535 g/cm³
• PKA: -5.19±0.20(Predicted)
• CAS DataBase Reference: N-(4-NITROPHENYL)MALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-NITROPHENYL)MALEIMIDE(4338-06-1)
• EPA Substance Registry System: N-(4-NITROPHENYL)MALEIMIDE(4338-06-1)

Safety Data

• Hazard Codes: Xi
• Statements: 22
• Safety Statements: 23-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 4338-06-1(Hazardous Substances Data)

Usage

General Description

N-(4-Nitrophenyl)maleimide is a chemical compound that belongs to the class of maleimides. It is a yellow crystalline solid that is commonly used in biochemical research as a thiol-reactive compound. It is known for its ability to react with thiol groups found in proteins, peptides, and other biomolecules, making it a useful tool for studying protein structure and function. N-(4-Nitrophenyl)maleimide is often used in protein modification and labeling experiments, as it forms stable adducts with thiol groups and allows for the study of thiol-containing proteins. Additionally, it has been used in the development of fluorescent probes and biologically active molecules. Its reactivity and versatility make it a valuable tool in various fields of research, including biochemistry and chemical biology.

Upstream product

• 36342-10-6 4-(4-nitrophenylamino)-4-oxobut-2-enoic acid 
• 941-69-5 N-phenyl-maleimide 
• 30186-41-5 1-(4-nitrophenyl)pyrrole-2-carbaldehyde 
• 36342-10-6 (Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid 
• 108-31-6 maleic anhydride 
• 100-01-6 4-nitro-aniline 
• 110-16-7 maleic acid 
• 37904-11-3 3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione 
• 80818-24-2 (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 

Downstream Products

• 60437-33-4 2-(2-amino-4-methyl-7-oxo-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-6-yl)-N-(4-nitro-phenyl)-acetamide 
• 70464-55-0 3ξ-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-34-3 2-(4-chloro-phenyl)-5-(4-nitro-phenyl)-3c-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 57703-45-4 2-(4-nitro-phenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 35216-29-6 2-(4-tert-butyl-phenyl)-5-(4-nitro-phenyl)-3t-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-29-6 2-(4-tert-butyl-phenyl)-5-(4-nitro-phenyl)-3c-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 57703-50-1 6,7-dimethyl-2-(4-nitro-phenyl)-4,9-di-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 70464-63-0 5-(4-nitro-phenyl)-3-(2,4,6-trimethyl-phenyl)-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-15-0 5-(4-nitro-phenyl)-2,3t-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-15-0 5-(4-nitro-phenyl)-2,3c-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70518-37-5 5-(4-nitro-phenyl)-2,3ξ-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-58-3 3ξ-(4-bromo-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-56-1 3ξ,5-bis-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-57-2 3ξ-(4-dimethylamino-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 

Relevant articles and documents

Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides. Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones

1,4-Diarylimidazoline 3-oxides react with N-arylmaleimides in benzene to give predominantly the corresponding endo adducts. Chiral imidazoline 3-oxides react diastereospecifically (cis configuration of the tetrahydroimidazo ring) and diastereoselectively to give cis-endo adducts. The effects of substituents on the aromatic ring of the maleimide was investigated. The presence of electron-withdrawing or releasing groups have minor effect on the total yields but more pronounced is the effect on the ratio of exo and endo diastereomers. The adducts undergo an interesting and unprecedented ring-opening in the presence of secondary amines to give deoxygenated 3-imidazoline 3-oxides instead of the expected double cis elimination products. Tertiary amines did not induce any reaction.

Exploiting: Exo and endo furan-maleimide Diels-Alder linkages for the functionalization of organoruthenium complexes

Diels-Alder cycloadditions involving furans and maleimides are extensively used in organic chemistry and materials synthesis. Given the promising advances of organoruthenium complexes in therapy, we explored the possibility of exploiting such Diels-Alder linkages as a mean to modulate their biological properties. This journal is

Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light

An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).