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

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

Uses

1. Used in Plastic Industry:
N-Benzylmaleimide is used as a plastic additive for enhancing the properties of plastics, such as improving their stability and durability.
2. Used in Pharmaceutical Industry:
N-Benzylmaleimide serves as a pharmaceutical intermediate, playing a crucial role in the development and synthesis of various drugs.
3. Used in Organic Synthesis:
As an important intermediate, N-Benzylmaleimide is utilized in organic synthesis for the creation of new compounds and molecules.
4. Used in Agrochemicals:
N-Benzylmaleimide is employed in the agrochemical industry for the development of pesticides and other agricultural chemicals.
5. Used in Dyestuff Industry:
N-Benzylmaleimide is also used as a key component in the production of dyes and dyestuff, contributing to the color and quality of the final products.

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

• 685543-77-5 trans-3-(benzylcarbamoyl)acrylic acid 
• 541-59-3 maleiimide 
• 100-51-6 benzyl alcohol 
• 15329-69-8 N-benzylmaleamic acid 
• 108-24-7 acetic anhydride 
• 133341-92-1 N-benzyl-3-chloropyrrolidine-2,5-dione 
• 85843-33-0 N-Benzyl-isomaleimid 
• 2592-95-2 benzotriazol-1-ol 
• 108-31-6 maleic anhydride 
• 100-46-9 benzylamine 
• 617-48-1 malic acid 
• 272449-67-9 (+/-)-(3aR,4S,7R,7aS)-2-benzyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 100-39-0 benzyl bromide 
• 134575-94-3 C₁₁H₁₁NO₃ 

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 
• 89143-32-8 1-benzyl-3-(piperidin-1-yl)pyrrolidine-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 
• 80818-39-9 N-benzyl-4,5-diphenyl-cis-1,2,3,6-tetrahydrophthalimide 
• 118458-36-9 N-benzyl-4,5-bis(trimethylsilyloxy)-cis-Δ⁴-tetrahydrophthalimide 
• 121942-29-8 Dithiocarbonic acid S-((3S,4R)-4-allyl-1-benzyl-2,5-dioxo-pyrrolidin-3-yl) ester O-methyl ester 
• 79632-02-3 2-benzyl-5α,6-dimethyl-8α-<(benzyloxy)methyl>-2,4β,5β,8β,9β-pentahydro-1H-isoindole-1,3-dione 
• 82071-85-0 N-Benzyl-7-bromo-1,4,5,6,7-pentachlorobicyclo<2.2.1>hept-5-ene-2,3-dicarboximide 
• 130999-07-4 N-benzyl-1,2,3,6-tetrahydro-3,6-bis(2-nitrophenyl)phthalimide 
• 129056-01-5 Dithiocarbonic acid S-((3S,4R)-1,4-dibenzyl-2,5-dioxo-pyrrolidin-3-yl) ester O-methyl ester 
• 132374-44-8 N-benzyl-α-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylthio)succinimide 
• 133707-74-1 6-Benzyl-4-ethoxy-3-methyl-5,7-dioxo-6,7-dihydro-5H-isoxazolo[4,5-f]isoindole-8-carboxylic acid ethyl ester 

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.

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

In the ionic liquids [Bmim][PF6] or [Bmim][BF4], a series of succinimide, maleimide and phthalimide derivatives were synthesized from corresponding anhydrides with a variety of primary amines in excellent yield.

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.

Thermally Sensitive Protecting Groups for Cysteine, and Manufacture and Use Thereof

In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.

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.).

Preparation method of medical intermediate N-benzyl-3-pyrroline

The invention discloses a preparation method of a medical intermediate N-benzyl-3-pyrroline. The method comprises the following steps: adding a proper amount of benzylamine, maleic anhydride and a reaction medium into a reaction flask, and stirring for reaction to obtain a diamide compound; and dissolving a diamide compound in tetrahydrofuran, dropwise adding a proper amount of 70% red aluminum solution, and reducing the diamide compound to obtain N-benzyl-3-pyrroline; The method is low in raw material cost, simple in process step, high in yield, small in pollution, high in product purity and suitable for industrial production.

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.

Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation

Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.

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.