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N-Benzylmaleimide

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CAS:1631-26-1
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CAS:1631-26-1
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CAS:1631-26-1
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  • 1-Benzylpyrrole-2,5-dione
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  • CAS:1631-26-1
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  • N-Benzylmaleimide
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  • 2022-02-10
  • CAS:1631-26-1
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  • N-Benzylmaleimide
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  • CAS:1631-26-1
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N-Benzylmaleimide Basic information
Product Name:N-Benzylmaleimide
Synonyms:1H-Pyrrole-2,5-dione, 1-(phenylmethyl)-;ASISCHEM D48963;AKOS MSC-0016;AKOS 90883;eimide;(2S)-2-[[[4-[2-(2-amino-4-oxo-1H-pteridin-6-yl)ethylamino]cyclohexyl]-oxomethyl]amino]pentanedioic acid;1-BENZYL-PYRROLE-2,5-DIONE;1-BENZYL-1H-PYRROLE-2,5-DIONE
CAS:1631-26-1
MF:C11H9NO2
MW:187.19
EINECS:216-631-1
Product Categories:N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Intermediates of Dyes and Pigments;PHARMACEUTICAL INTERMEDIATES;Heterocycles;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
Mol File:1631-26-1.mol
N-Benzylmaleimide Structure
N-Benzylmaleimide Chemical Properties
Melting point 70 °C (lit.)
Boiling point 177 °C / 20mmHg
density 1 g/cm3
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
pka-2.21±0.20(Predicted)
form powder to crystal
color White to Almost white
Water Solubility Insoluble
BRN 135801
InChIInChI=1S/C11H9NO2/c13-10-6-7-11(14)12(10)8-9-4-2-1-3-5-9/h1-7H,8H2
InChIKeyMKRBAPNEJMFMHU-UHFFFAOYSA-N
SMILESN1(CC2=CC=CC=C2)C(=O)C=CC1=O
CAS DataBase Reference1631-26-1(CAS DataBase Reference)
NIST Chemistry ReferenceN-benzylmaleimide(1631-26-1)
Safety Information
Hazard Codes C,T
Risk Statements 34-25-20/21
Safety Statements 26-36/37/39-45
RIDADR UN 1759 8/PG 2
WGK Germany 3
Hazard Note Irritant
HazardClass 8
PackingGroup III
HS Code 29251900
Storage Class8A - Combustible corrosive hazardous materials
Hazard ClassificationsEye Dam. 1
Skin Corr. 1B
MSDS Information
ProviderLanguage
1-Benzyl-1H-pyrrole-2,5-dione English
ACROS English
SigmaAldrich English
ALFA English
N-Benzylmaleimide Usage And Synthesis
Chemical Propertiesoff-white to light yellow
UsesN-Benzylmaleimide is used as plastic additive, Pharmaceutical Intermediates. It is an important raw material intermediate used in organic Synthesis, Pharmaceuticals, Agrochemicals Dyestuff.
General DescriptionN-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.
Synthesis
Maleic anhydride

108-31-6

Benzylamine

100-46-9

N-Benzylmaleimide

1631-26-1

GENERAL PROCEDURE: At room temperature, benzylamine (17 mmol) was slowly added dropwise to a solution of maleic anhydride (20 mmol) dissolved in acetic acid (10 mL) to form a suspension. Subsequently, the reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in chloroform (100 mL) and extracted by partition with deionized water (30 mL). The aqueous phase was further extracted with chloroform (3 x 50 mL). All organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate (30 mL) and brine (30 mL). The organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. Finally, the concentrated residue was purified by silica gel column chromatography to obtain N-benzylmaleimide.

References[1] Journal of Chemical Research - Part S, 1998, # 5, p. 272 - 273
[2] Journal of the Chinese Chemical Society, 2009, vol. 56, # 4, p. 839 - 842
[3] Synthesis, 2004, # 7, p. 995 - 998
[4] Tetrahedron Letters, 1997, vol. 38, # 46, p. 8089 - 8092
[5] Tetrahedron Asymmetry, 2008, vol. 19, # 18, p. 2115 - 2118
N-Benzylmaleimide Preparation Products And Raw materials
Raw materialsMaleic anhydride-->Benzylamine
Preparation Products5-NITROFURFURYL ALCOHOL
Tag:N-Benzylmaleimide(1631-26-1) Related Product Information
Succinimide Bismaleimide O-Phthalimide Benzyl nicotinate Benzyl chloride Benzyl alcohol N-Ethylmaleimide Maleimide Benzyl benzoate Pyrrole N-Phenylmaleimide N-Benzyl-N-methylethanolamine N-Phenethylbenzamide DIALIFOS Benzyl 1-((4-METHYLPHENYL)METHYL)-1H-PYRROLE-2,5-DIONE (S)-(-)-N-(1-PHENYLETHYL)MALEIMIDE 1-((4-METHOXYPHENYL)METHYL)-1H-PYRROLE-2,5-DIONE

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