40349-49-3

Basic information

• Product Name: 4-maleimidobenzoic acid methyl ester
• Synonyms: 4-(2,5-dioxo-1-pyrrolyl)benzoic acid methyl ester;4-maleimidobenzoic acid methyl ester;methyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate;methyl 4-(2,5-dioxopyrrol-1-yl)benzoate
• CAS NO: 40349-49-3
• Molecular Formula: C₁₂H₉NO₄
• Molecular Weight: 231.21
• Mol File: 40349-49-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 396.7°C at 760 mmHg
• Flash Point: 193.7°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 1.68E-06mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 4-maleimidobenzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-maleimidobenzoic acid methyl ester(40349-49-3)
• EPA Substance Registry System: 4-maleimidobenzoic acid methyl ester(40349-49-3)

Safety Data

• Hazardous Substances Data: 40349-49-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H9NO4/c1-17-12(16)8-2-4-9(5-3-8)13-10(14)6-7-11(13)15/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 29305-46-2 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 108-31-6 maleic anhydride 
• 17057-04-4 N-(4-carboxyphenyl)maleimide 
• 125407-30-9 (Z)-4-((4-(methoxycarbonyl)phenyl)amino)-4-oxobut-2-enoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 1229020-49-8 C₃₁H₄₅N₃O₅ 

Relevant articles and documents

Biologically active thio-pyrimidinones from base-catalyzed thiol-ene coupling with maleimides

The synthesis of 2-thiopyrimidinones through thiol-ene coupling is reported here, resulting in 35 unpublished molecules. Thiopyrimidinones may exhibit one up to three tautomeric forms, and favoring the thiol tautomer is favored is the key to success of this reaction. Five compounds from all obtained products, those substituted with a carbonyl ester portion in the side chain, were chosen to be tested in a preliminary evaluation for human aldose reductase inhibition. All tested compounds showed an inhibition percentage equal to or >60%.

Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives

In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.

Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis

Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).