1631-26-1

Basic information

• Product Name: N-Benzylmaleimide
• Synonyms: 1H-Pyrrole-2,5-dione, 1-(phenylmethyl)-;ASISCHEM D48963;AKOS MSC-0016;AKOS 90883;1-BENZYL-PYRROLE-2,5-DIONE;1-BENZYL-1H-PYRROLE-2,5-DIONE;1-((PHENYL)METHYL)-1H-PYRROLE-2,5-DIONE;N-BENZYLMALEIMIDE
• CAS NO: 1631-26-1
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• EINECS: 216-631-1
• Product Categories: Intermediates of Dyes and Pigments;PHARMACEUTICAL INTERMEDIATES;Heterocycles;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 1631-26-1.mol
• Article Data: 72

Chemical Properties

• Melting Point: 70 °C(lit.)
• Boiling Point: 177 °C / 20mmHg
• Flash Point: 157.9 °C
• Appearance: /
• Density: 1 g/cm3
• Vapor Pressure: 9.61E-05mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -2.21±0.20(Predicted)
• Water Solubility: Insoluble
• BRN: 135801
• CAS DataBase Reference: N-Benzylmaleimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylmaleimide(1631-26-1)
• EPA Substance Registry System: N-Benzylmaleimide(1631-26-1)

Safety Data

• Hazard Codes: C,T
• Statements: 34-25-20/21
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1631-26-1(Hazardous Substances Data)

Usage

Chemical Properties

off-white to light yellow

Uses

N-Benzylmaleimide is used as plastic additive, Pharmaceutical Intermediates. It is an important raw material intermediate used in organic Synthesis, Pharmaceuticals, Agrochemicals Dyestuff.

General Description

N-Benzylmaleimide is an N-substituted maleimide and its microwave-mediated facile and fast synthesis has been described. Radical and anionic copolymerization of N-benzylmaleimide with optically active N-(L-menthoxycarbonylmethyl)maleimide has been reported. Base-catalyzed asymmetric cycloaddition of anthrone with N-benzylmaleimide was studied in the presence of C2-chiral pyrrolidines. Stereoselctive iridium-catalyzed double incorporation reaction of styrene with N-benzylmaleimide affords cyclic product.

InChI:InChI=1/C11H9NO2/c13-10-6-7-11(14)12(10)8-9-4-2-1-3-5-9/h1-7H,8H2

Upstream product

• 541-59-3 maleiimide 
• 100-51-6 benzyl alcohol 
• 15329-69-8 N-benzylmaleamic acid 
• 108-31-6 maleic anhydride 
• 100-46-9 benzylamine 
• 932-90-1 Benzaldoxime 
• 100-52-7 benzaldehyde 
• 2051-97-0 1-benzyl-1H-pyrrole 
• 903758-94-1 C₁₂H₁₃NO₃ 
• 134575-94-3 C₁₁H₁₁NO₃ 
• 100-39-0 benzyl bromide 
• 272449-67-9 (+/-)-(3aR,4S,7R,7aS)-2-benzyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 617-48-1 malic acid 
• 85843-33-0 N-Benzyl-isomaleimid 

Downstream Products

• 64251-55-4 2-benzyl-4,7-dimethyl-3a,4,7,7a-tetrahydro-4,7-epioxido-isoindole-1,3-dione 
• 34081-76-0 1'-benzyl-2',5'-dioxo-[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine 
• 89143-20-4 1'-benzyl-[1,3'-bipyrrolidine]-2',5'-dione 
• 104139-64-2 5-(1-Benzyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: Highly efficient construction of azaspiro[4.4]nonenes

Phosphine-catalyzed [4+1] annulation of electron-deficient 1,3-dienes or 1,3-azadienes with maleimides has been successfully developed under very mild conditions, providing a convenient and highly efficient method for constructing 2-azaspiro[4.4]nonenes and 1,7-diazaspiro[4.4]nonenes. This reaction represents the first example of [4+1] cyclization between electron-deficient 4π-conjugated systems and non-allylic phosphorus ylides.

An efficient protocol for the synthesis of N-Alkyl- and N-Arylimides using the lewis acidic ionic liquid choline chloride-2ZnCl2

Lewis acidic ionic liquid choline chloride-2ZnCl2 is shown to be for the first time an excellentmedium and efficient catalyst for the synthesis of N-alkyl- and N-arylimides in good yields under mild conditions.

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.

Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents

The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).