Production Method 1

555-59-9

941-69-5

Reaction Conditions

1.1 Catalysts: Sulfobetaine methacrylate Solvents: Methyl isobutyl ketone ,  Water ;  20 s, 100 °C; 35 s, 100 °C; 150 s, 100 °C

Reference

Preparation of N-substituted maleimide in microchannel reactor

, China, , ,

Production Method 2

108-31-6

941-69-5

Reaction Conditions

1.1 Solvents: Acetic acid ;  10 min, rt
1.2 Reagents: Sulfuric acid ;  rt → 60 °C; 45 min, 60 °C; 60 °C → rt
1.3 Reagents: Water ;  cooled
1.4 Reagents: Sodium bicarbonate Solvents: Water ;  10 min

Reference

DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: facile access to dinitrogen-fused heterocycles

Jia, Qianfa; Chen, Lei; Yang, Gongming; Wang, Jian; Wei, Jia; et al, Tetrahedron Letters, 2015, 56(52), 7150-7153

Production Method 3

108-31-6

941-69-5

Reaction Conditions

1.1 Solvents: Acetic acid ;  10 min, rt
1.2 Reagents: Sulfuric acid Solvents: Water ;  rt → 60 °C; 45 min, 60 °C; 60 °C → rt; cooled
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  10 min, rt

Reference

Synthesis of substituted N-aryl pyrrolo-quinolines and study of their antimicrobial activities

Deshmukha, Ganesh B.; Patila, Nilesh S.; Gaikwada, Vishwas B.; Bholeb, Avinash D.; Patila, Sambhaji V., Journal of Chemical and Pharmaceutical Research, 2014, 6(8), 393-399

Production Method 4

2851450-77-4

941-69-5

Reaction Conditions

1.1 Solvents: Xylene ;  4 h, 150 °C

Reference

Green preparation of N-phenylmaleimide

, China, , ,

Production Method 5

108-31-6

941-69-5

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid ,  Copper sulfate Solvents: Dimethylformamide ,  Toluene

Reference

Preparation of N-substituted maleimides.

, Japan, , ,

Production Method 6

108-31-6

941-69-5

Reaction Conditions

1.1 Solvents: 1-Butyl-3-methylimidazolium hexafluorophosphate ;  20 min, 140 °C

Reference

Organic reactions in ionic liquids: Ionic liquid-promoted efficient synthesis of N-alkyl and N-arylimides

Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo, Synthesis, 2004, (7), 995-998

Production Method 7

555-59-9

941-69-5

Reaction Conditions

1.1 Reagents: Methanol Solvents: Methyl isobutyl ketone ;  50 min, 20 °C
1.2 40 min, 60 °C

Reference

Preparation of N-substituted maleimide in microchannel continuous flow reactor

, China, , ,

Production Method 8

108-31-6

941-69-5

Reaction Conditions

1.1 Solvents: Xylene ;  rt → 80 °C; 0.5 h, 80 °C; 1 h, 80 °C
1.2 Reagents: Hydroquinone Catalysts: Phosphoric acid Solvents: Xylene ,  Water ;  rt → 65 °C; 1.5 h, 65 °C

Reference

Synthesis of N-phenylmaleimide by decompressed azeotropic method

Wang, Dong-hui; Feng, Ya-qing; Liang, Zu-pei; Shi, Da-xin, Huaxue Gongye Yu Gongcheng (Tianjin, 2005, 22(6), 427-429

Production Method 9

108-31-6

941-69-5

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid ,  2,5-Dimethylbenzenesulfonic acid Solvents: Benzene ,  Tetrahydrofuran ;  rt → 85 °C; 85 °C → reflux; reflux; 60 min, reflux

Reference

One-step synthesis of N-phenyl maleimide

, China, , ,

Production Method 10

108-31-6

941-69-5

Reaction Conditions

1.1 Catalysts: Silica ,  Phosphoric acid Solvents: Xylene
1.2 Catalysts: Triethylamine ,  Zinc acetate ,  2,4-Dimethyl-6-tert-butylphenol ;  neutralized
1.3 5 min
1.4 5 min; 140 °C; 6 h, 140 °C

Reference

Method for the preparation of N-substituted maleimide

, World Intellectual Property Organization, , ,

Production Method 11

108-31-6

941-69-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Silica ,  Phosphoric acid Catalysts: Zinc acetate ,  2,4-Dimethyl-6-tert-butylphenol Solvents: Xylene
1.2 5 min
1.3 5 min; 6 h, 140 °C

Reference

Method for preparing N-substituted maleimide

, Korea, , ,

Production Method 12

555-59-9

941-69-5

Reaction Conditions

1.1 Reagents: Acetic anhydride Catalysts: Sodium acetate Solvents: Acetic anhydride ;  2 h, reflux; cooled
1.2 Reagents: Water

Reference

N-Phenyl and N-phenylalkyl-maleimides acting against Candida spp.: Time-to-kill, stability, interaction with maleamic acids

Sortino, Maximiliano; Cechinel Filho, Valdir; Correa, Rogerio; Zacchino, Susana, Bioorganic & Medicinal Chemistry, 2008, 16(1), 560-568

Production Method 13

108-31-6

941-69-5

Reaction Conditions

1.1 Reagents: 1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride (1:1) Solvents: Toluene

Reference

Preparation of (poly)maleimides as monomers

, Japan, , ,

Production Method 14

36342-11-7

941-69-5

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Toluene ,  Water

Reference

Preparation of N-substituted maleimides with low discoloration

, Japan, , ,

Production Method 15

108-31-6

941-69-5

Reaction Conditions

1.1 Reagents: Cupric acetate ,  Triphenyl phosphorotrithioite Solvents: Dimethylformamide ,  Toluene

Reference

Preparation of N-substituted maleimides

, Japan, , ,

Production Method 16

108-31-6

941-69-5

Reaction Conditions

1.1 Solvents: Acetone ;  1 h, rt; 1 h, 40 °C
1.2 Reagents: Cobalt diacetate Catalysts: Triethylamine Solvents: Acetone ,  Acetic anhydride ;  3 h, 40 °C

Reference

Synthesis, antimicrobial and corrosion-inhibiting activities of N-substituted phenyl maleimide

Yang, Fengke; Jiang, Ping, Qingdao Keji Daxue Xuebao, 2011, 32(1), 30-33

Production Method 17

108-31-6

941-69-5

Reaction Conditions

1.1 Catalysts: 1-Butyl-3-methylimidazolium hexafluorophosphate Solvents: 1-Butyl-3-methylimidazolium hexafluorophosphate ;  20 min, 110 °C

Reference

Synthesis of imide derivatives

, China, , ,

N-Phenylmaleimide Raw materials

• Maleanilic Acid
• 3-chloro-1-phenyl-2,5-Pyrrolidinedione
• 3a,4,7,7a-Tetrahydro-2-phenyl-4,7-imino-1H-isoindole-1,3(2H)-dione
• 2,5-dihydrofuran-2,5-dione

N-Phenylmaleimide Preparation Products

• N-Phenylmaleimide (941-69-5)

• 1. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 2. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 3. Evolutionary approaches in protein engineering towards biomaterial construction
  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
• 4. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
• 5. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolines Phenylpyrrolines
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

N-Phenylmaleimide (CAS No. 941-69-5): A Versatile Chemical Intermediate in Modern Pharmaceutical and Material Science Research

N-Phenylmaleimide, with the chemical formula C?H?NO? and CAS number 941-69-5, is a significant compound in the realm of organic chemistry and has garnered considerable attention due to its diverse applications. This heterocyclic compound, characterized by an imide functional group attached to a phenyl ring, exhibits unique reactivity that makes it invaluable in synthetic chemistry, particularly in the development of pharmaceuticals and advanced materials.

The utility of N-Phenylmaleimide stems from its ability to participate in various chemical reactions, including Michael additions, Diels-Alder reactions, and Michael additions, which are pivotal in constructing complex molecular architectures. Its structure allows for facile functionalization, making it a preferred intermediate in the synthesis of bioactive molecules. Recent advancements in medicinal chemistry have highlighted its role in designing novel therapeutic agents targeting various diseases.

In the pharmaceutical industry, N-Phenylmaleimide has been explored as a key building block for drugs that interact with biological macromolecules. For instance, its ability to form covalent bonds with proteins has been leveraged in the development of protease inhibitors and kinase inhibitors. These inhibitors are crucial in treating conditions such as cancer, inflammation, and infectious diseases. The compound's reactivity with thiols present in proteins allows for the creation of stable adducts, which can modulate enzyme activity and serve as scaffolds for drug design.

One of the most compelling applications of N-Phenylmaleimide is in the field of material science. Its incorporation into polymers and coatings enhances their mechanical properties and thermal stability. Researchers have utilized this compound to develop advanced polymers that exhibit self-healing capabilities, making them suitable for applications in aerospace and automotive industries where durability is paramount. Additionally, its photochemical properties have been exploited to create light-sensitive materials used in optoelectronic devices.

The synthesis of N-Phenylmaleimide typically involves the reaction of maleic anhydride with aniline under controlled conditions. This reaction is straightforward yet requires precise control over temperature and stoichiometry to achieve high yields. Recent improvements in synthetic methodologies have focused on greener approaches, utilizing catalytic systems that minimize waste and energy consumption. Such innovations align with the growing emphasis on sustainable chemistry practices.

Recent research has also delved into the biological activities of derivatives of N-Phenylmaleimide. Studies have shown that certain modifications of this core structure can enhance its binding affinity to target proteins while reducing off-target effects. This has led to the discovery of novel compounds with potent therapeutic properties. For example, derivatives of N-Phenylmaleimide have been investigated for their potential as antiviral agents, showing promise in preclinical studies against various viral infections.

The compound's interaction with biological systems has also been studied from a mechanistic perspective. Understanding how N-Phenylmaleimide binds to proteins at the atomic level has provided insights into drug design principles. Techniques such as X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy have been instrumental in elucidating these interactions. These structural insights have guided the development of next-generation drugs with improved efficacy and safety profiles.

In conclusion, N-Phenylmaleimide (CAS No. 941-69-5) is a multifaceted compound with broad applications across pharmaceuticals and material science. Its unique chemical properties make it an indispensable tool for synthetic chemists and researchers working on cutting-edge technologies. As our understanding of its reactivity and biological interactions continues to grow, so too will its role in developing innovative solutions to global challenges.

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