N-Methylmaleimide Chemical Properties

Melting point:

94-96 °C (lit.)

Boiling point:

208.19°C (rough estimate)

Density 

1.3113 (rough estimate)

refractive index 

1.4260 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

-2.18±0.20(Predicted)

form 

Crystals

color 

Light yellow

Water Solubility 

Slightly soluble in water.

BRN 

108550

InChI

InChI=1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3

InChIKey

SEEYREPSKCQBBF-UHFFFAOYSA-N

SMILES

N1(C)C(=O)C=CC1=O

CAS DataBase Reference

930-88-1(CAS DataBase Reference)

NIST Chemistry Reference

N-Methylmaleimide(930-88-1)

Safety Information

Hazard Codes 

C

Risk Statements 

22-34-43-25-20/21

Safety Statements 

26-36/37/39-45

RIDADR 

UN 1759 8/PG 2

WGK Germany 

3

RTECS 

ON5600000

F 

10-21

HazardClass 

6.1

PackingGroup 

II

HS Code 

29241990

MSDS

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

N-Methylmaleimide Usage And Synthesis

Chemical Properties

light yellow crystals

Uses

N-Methylmaleimide is an electron deficient olefin that acts as a thiol-blocking reagent.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013

Synthesis

GENERAL METHOD: Methylamine hydrochloride (19.1 g, 0.30 mol) was added to a solution of acetic acid (40 mL) containing maleic anhydride (20 g, 0.20 mol) and potassium acetate (30.0 g, 0.30 mol) and stirred thoroughly. The mixture was heated to reflux temperature (110 °C) and the reaction was maintained for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 25-30 °C. Subsequently, the reaction mixture was slowly poured into pre-cooled sodium bicarbonate solution (100 mL) and extracted with diethyl ether (3 x 70 mL). The organic layers were combined, washed with brine solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give N-methylmaleimide (6.89 g, 30% yield).

Purification Methods

Crystallise the imide three times from diethyl ether. Dry it in vacuo.[Beilstein 21/10 V 5.]

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4577 - 4580

N-Methylmaleimide(930-88-1)Related Product Information

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