N-METHOXYCARBONYLMALEIMIDE

N-METHOXYCARBONYLMALEIMIDE Property

Melting point:

63-65 °C

Boiling point:

242.5±23.0 °C(Predicted)

Density 

1.496±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Chloroform

form 

Solid

pka

-3.17±0.20(Predicted)

color 

Off-White to Pink

BRN 

1450638

InChI

InChI=1S/C6H5NO4/c1-11-6(10)7-4(8)2-3-5(7)9/h2-3H,1H3

InChIKey

LLAZQXZGAVBLRX-UHFFFAOYSA-N

SMILES

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

Safety

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

29251900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

N-METHOXYCARBONYLMALEIMIDE Chemical Properties,Usage,Production

Chemical Properties

Off-White Cyrstalline Solid

Uses

N-(Methoxycarbonyl) Maleimide (cas# 55750-48-6) is a compound useful in organic synthesis.

Synthesis

To a solution of ethyl acetate (120 mL) of maleimide (6.35 g, 65.4 mmol) was sequentially added N-methylmorpholine (NMM, 8.6 mL, 78.5 mmol) and methyl chloroformate (6.0 mL, 78.5 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 30 min, then brought to room temperature and continued stirring for 1 h. The reaction was completed by filtration. Upon completion of the reaction, the solid was collected by filtration and the filtrate was concentrated under reduced pressure. The concentrated residue was dissolved in dichloromethane, filtered through a silica gel column and eluted with dichloromethane to remove red impurities. The eluate was concentrated and the resulting solid was ground with a solvent mixture of ethyl acetate and petroleum ether to give a final white solid of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate (9.0 g, 88% yield).

References

[1] Chemistry Letters, 2012, vol. 41, # 3, p. 313 - 315
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7890 - 7901
[3] Patent: WO2017/46658, 2017, A1. Location in patent: Page/Page column 149; 150
[4] Journal of Fluorine Chemistry, 2013, vol. 152, p. 173 - 181
[5] Journal of the American Chemical Society, 2008, vol. 130, # 34, p. 11288 - 11289