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

InChI

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

InChIKey

MKRBAPNEJMFMHU-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)C(=O)C=CC1=O

CAS DataBase Reference

1631-26-1(CAS DataBase Reference)

NIST Chemistry Reference

N-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

MSDS

• Language:English Provider:1-Benzyl-1H-pyrrole-2,5-dione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Benzylmaleimide Usage And Synthesis

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.

Synthesis

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(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
• 4-(DICHLOROMETHYL)PYRIDINE HCL
• 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