ChemicalBook--->CAS DataBase List--->55750-48-6

55750-48-6

55750-48-6 Structure

55750-48-6 Structure
IdentificationBack Directory
[Name]

N-METHOXYCARBONYLMALEIMIDE
[CAS]

55750-48-6
[Synonyms]

Einecs 259-792-3
N-(CarboMethoxy)MaleiMide
N-METHOXYCARBONYLMALEIMIDE
N-methoxycarbonylmaleimide 98%
N-Methoxycarbonylmaleimide≥ 98%(N)
N-MethoxycarbonylMaleiMide >=97.0% (N)
Methyl 2,5-dioxo-2H-pyrrole-1(5H)-carboxylate
2,5-Dioxo-3-pyrroline-1-carboxylic acid methyl ester
Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate
methyl 2,5-dihydro-2,5-dioxo-1H-pyrrole-1-carboxylate
2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-carboxylic acid methyl ester
2,5-Dioxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid methyl ester
1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-2,5-dioxo-, Methyl ester
[EINECS(EC#)]

259-792-3
[Molecular Formula]

C6H5NO4
[MDL Number]

MFCD00042755
[MOL File]

55750-48-6.mol
[Molecular Weight]

155.11
Chemical PropertiesBack Directory
[Appearance]

Off-White Cyrstalline Solid
[Melting point ]

63-65 °C
[Boiling point ]

242.5±23.0 °C(Predicted)
[density ]

1.496±0.06 g/cm3(Predicted)
[storage temp. ]

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
Hazard InformationBack Directory
[Chemical Properties]

Off-White Cyrstalline Solid
[Uses]

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

Maleimide

541-59-3

Methyl chloroformate

79-22-1

N-METHOXYCARBONYLMALEIMIDE

55750-48-6

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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P271-P261-P280
[Safety Statements ]

22-24/25
[WGK Germany ]

3
[F ]

10
[HS Code ]

29251900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Eye Irrit. 2
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Petroleum ether-->Methyl chloroformate-->Maleimide-->4-Methylmorpholine
[Preparation Products]

Maleimido-Tri(Ethylene Glycol)-Propionic Acid
Spectrum DetailBack Directory
[Spectrum Detail]

N-METHOXYCARBONYLMALEIMIDE(55750-48-6)1HNMR
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