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N-Phenylmaleimide

Base Information
  • Chemical Name:N-Phenylmaleimide
  • CAS No.:941-69-5
  • Molecular Formula:C10H7NO2
  • Molecular Weight:173.171
  • Hs Code.:2925.19
  • European Community (EC) Number:213-382-0
  • NSC Number:8183
  • UN Number:2811
  • UNII:9U9KT462VW
  • DSSTox Substance ID:DTXSID0041274
  • Nikkaji Number:J7.180C
  • Wikidata:Q27273236
  • ChEMBL ID:CHEMBL76012
  • Mol file:941-69-5.mol
N-Phenylmaleimide

Synonyms:N-phenylmaleimide

Suppliers and Price of N-Phenylmaleimide
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • N-Phenylmaleimide
  • 2.5g
  • $ 85.00
  • TRC
  • N-Phenylmaleimide
  • 250mg
  • $ 50.00
  • TCI Chemical
  • N-Phenylmaleimide >98.0%(GC)
  • 500g
  • $ 160.00
  • TCI Chemical
  • N-Phenylmaleimide >98.0%(GC)
  • 25g
  • $ 30.00
  • TCI Chemical
  • N-Phenylmaleimide >98.0%(GC)
  • 100g
  • $ 70.00
  • Sigma-Aldrich
  • N-Phenylmaleimide 97%
  • 100g
  • $ 139.00
  • Sigma-Aldrich
  • N-Phenylmaleimide 97%
  • 25g
  • $ 50.20
  • Oakwood
  • N-Phenylmaleimide 95+%
  • 1g
  • $ 10.00
  • Oakwood
  • N-Phenylmaleimide 95+%
  • 25g
  • $ 32.00
  • Matrix Scientific
  • 1-Phenyl-2,5-dihydro-1H-pyrrole-2,5-dione 97%
  • 50g
  • $ 151.00
Total 158 raw suppliers
Chemical Property of N-Phenylmaleimide
Chemical Property:
  • Appearance/Colour:yellow crystalline powder or needles 
  • Vapor Pressure:0.00121mmHg at 25°C 
  • Melting Point:85-87 °C(lit.) 
  • Refractive Index:1.629 
  • Boiling Point:299.26 °C at 760 mmHg 
  • PKA:-0.81±0.20(Predicted) 
  • Flash Point:136.835 °C 
  • PSA:37.38000 
  • Density:1.329 g/cm3 
  • LogP:1.18100 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:815g/l insoluble 
  • Water Solubility.:Soluble in water (slightly ), methanol, ethanol, and benzene. 
  • XLogP3:1.1
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:1
  • Exact Mass:173.047678466
  • Heavy Atom Count:13
  • Complexity:246
  • Transport DOT Label:Poison
Purity/Quality:

98% *data from raw suppliers

N-Phenylmaleimide *data from reagent suppliers

Safty Information:
  • Pictogram(s): ToxicT,IrritantXi 
  • Hazard Codes:T,Xi,N 
  • Statements: 25-36/37/38-23/24/25-50-43-41-38 
  • Safety Statements: 45-24/25-36/37/39-26-61-39-36/37 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:C1=CC=C(C=C1)N2C(=O)C=CC2=O
  • General Description N-Phenylmaleimide (PMI) is a reactive dienophile commonly used in Diels-Alder reactions, as demonstrated in studies involving the synthesis of benzotriazolylsuccinimides, cobalt dithiolene complexes, and thieno[2,3-c]pyrrole cycloadducts. It readily participates in condensation and cycloaddition reactions, often under thermal conditions, to form structurally diverse products, including succinimide derivatives, metal complexes, and fused heterocycles. Its versatility in organic synthesis highlights its utility in constructing complex molecular frameworks for applications in materials science and pharmaceuticals.
Technology Process of N-Phenylmaleimide

There total 53 articles about N-Phenylmaleimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With sulfuric acid; In dimethyl sulfoxide; toluene; Heating;
DOI:10.1021/jp9905474
Guidance literature:
aniline; With 2,4-dimethyl-6-tert-butylphenol; triethylamine; phosphoric acid; zinc diacetate; In xylene; for 0.0833333h;
maleic anhydride; In xylene; at 140 ℃; for 6h; Product distribution / selectivity;
Refernces

Synthesis of benzotriazolylsuccinimides in melt

10.1007/s11172-008-0063-2

The research focuses on the synthesis and study of benzotriazolylsuccinimides, which are based on benzotriazole (Bt) and maleimides. The experiments involved the condensation of Bt with N-phenylmaleimide (PMI) in a melt at temperatures ranging from 120 to 220 °C. The reaction was conducted in a fluoroplast cup to prevent side reactions such as homopolymerization of maleimides. The products were analyzed using 1H and 13C NMR spectroscopy, which confirmed the formation of both (benzotriazol-1-yl) and (benzotriazol-2-yl)succinimides, with the latter being a minor product. Fourier-transform IR spectroscopy was also used to record the spectra of the synthesized compounds. The reactants included Bt, PMI, and various bismaleimides such as N,N'-hexamethylenebimaleimide (HMBMI), N,N'-methylene(4,4'-diphenyl)bimaleimide (MDPBMI), and N,N'-oxido(4,4'-diphenyl)bimaleimide (ODPBMI). The analyses showed that the reaction could proceed through two paths, leading to the formation of both types of succinimides, and also indicated the presence of residual maleimide fragments, suggesting the reaction was not complete under the studied conditions.

CpCo1-mediated Diels-Alder reaction forming dimerie 1,3-dithiol-2-one derivative with spiro structure and successive formation of novel cobalt dithiolene complex

10.1246/cl.2008.1032

The research focuses on the synthesis of novel cobalt dithiolene complexes using a CpCoI-mediated Diels–Alder reaction. The purpose of the study was to develop a method for forming dimeric 1,3-dithiol-2-one derivatives with a spiro structure and subsequently generate new CpCo(dithiolene) complexes. The key chemicals used in the process include 4,5-bis(bromomethyl)-1,3-dithiol-2-one (1), CpCo(CO)2 (2), and N-phenylmaleimide. The researchers found that the reaction of 1 with CpCo(CO)2 under thermal conditions led to the formation of a dimeric 1,3-dithiol-2-one derivative (3) and a new CpCo(dithiolene) complex (4). The study concluded that CpCoI species not only facilitate the Diels–Alder reaction but also enable the successive formation of CpCo(dithiolene) complexes, providing a one-step synthesis method for these compounds, which are useful for syntheses of TTF derivatives and metal dithiolene complexes.

Thieno<2,3-c>pyrroles: Synthesis, Diels-ALder Reaction, and Synthetic Utility

10.1021/jo00295a038

The research focuses on the synthesis and chemical reactions of thieno[2,3-c]pyrroles. The authors developed a novel method for synthesizing these compounds through a retro-malonate addition reaction, starting from 3-methyl-2-thiophenecarboxaldehyde and diethyl malonate. They also explored the Diels-Alder reactions of thieno[2,3-c]pyrroles with reactive dienophiles such as N-phenylmaleimide and dimethyl acetylenedicarboxylate, leading to the formation of cycloadducts. The study includes the synthesis of various N-substituted thieno[2,3-c]pyrroles and their subsequent reactions to produce compounds like benzo[b]thiophene. The research also investigates the free-energy barriers of inversion of the imine nitrogens in the cycloadducts using variable-temperature 'H NMR spectroscopy. The study provides valuable insights into the synthetic utility and reactivity of thieno[2,3-c]pyrroles, contributing to the field of organic chemistry and potentially to the development of new pharmaceuticals and electroconducting polymers.

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