6633-22-3

Basic information

• Product Name: 1-(4-FLUORO-PHENYL)-PYRROLE-2,5-DIONE
• Synonyms: N-(4-FLUORO-PHENYL)MALEIMIDE;ASISCHEM N13878;1-(4-FLUOROPHENYL)-1H-PYRROLE-2,5-DIONE;1-(4-FLUORO-PHENYL)-PYRROLE-2,5-DIONE;AKOS MSC-0027;1-(4-Fluorophenyl)-3-pyrroline-2,5-dione;1H-Pyrrole-2,5-dione, 1-(4-fluorophenyl)-
• CAS NO: 6633-22-3
• Molecular Formula: C₁₀H₆FNO₂
• Molecular Weight: 191.16
• Mol File: 6633-22-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: 154.0 to 158.0 °C
• Boiling Point: 317.8°C at 760 mmHg
• Flash Point: 146°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0.000375mmHg at 25°C
• Refractive Index: 1.605
• PKA: -0.74±0.20(Predicted)
• CAS DataBase Reference: 1-(4-FLUORO-PHENYL)-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-FLUORO-PHENYL)-PYRROLE-2,5-DIONE(6633-22-3)
• EPA Substance Registry System: 1-(4-FLUORO-PHENYL)-PYRROLE-2,5-DIONE(6633-22-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 6633-22-3(Hazardous Substances Data)

Usage

Uses

1-(4-Fluorophenyl)-1H-pyrrole-2,5-dione is a maleimide derivative with antimicrobial and antifungal activity.

InChI:InChI=1/C10H6FNO2/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(12)14/h1-6H

Upstream product

• 60252-79-1 4-[(4-fluorophenyl)amino]-4-oxobut-2-enoic acid 
• 371-40-4 4-fluoroaniline 
• 780-05-2 (Z)-4-((4-fluorophenyl)amino)-4-oxobut-2-enoic acid 
• 108-31-6 maleic anhydride 
• 52326-08-6 N-sulfinyl-4-fluoroaniline 

Downstream Products

• 134310-35-3 3-<5-(3-nitrophenyl)-2-furyl>-5-(4-fluorophenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134310-36-4 3-(2,5-dimethyl-3-furyl)-5-(4-fluorophenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 146815-06-7 2-Methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(4-fluorophenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 146815-12-5 2-Methyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(4-fluorophenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 146815-16-9 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(4-fluorophenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 112313-20-9 1-(4-Fluoro-phenyl)-3-phenoxy-pyrrolidine-2,5-dione 
• 1004792-57-7 methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(1-naphthyl)-5-(p-fluorophenyl)-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate 
• 1258326-12-3 C₂₄H₁₆FNO₄ 
• 354150-92-8 (15S)-13-(4-fluorophenyl)-10-hydroxy-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione 

Relevant articles and documents

Photochemical Reaction of N,N-Dimethylanilines with N-Substituted Maleimides Utilizing Benzaldehyde as the Photoinitiator

Photoorganocatalysis constitutes a powerful domain of photochemistry and organic synthesis. The scaffold of pyrrolo[3,4-c]quinolinoles exhibits interesting and potent inhibition against various enzymes, making them really promising pharmaceutical targets. Herein, we describe a photochemical methodology for the reaction of N,N-dimethylanilines with N-substituted maleimides, utilizing benzaldehyde as the photoinitiator. A variety of substituted N,N-dimethylanilines and N-substituted maleimides were converted into the corresponding adducts in moderate to high yields.

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Application of maleimide compound as chitin synthase inhibitor

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.