| Identification | Back 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 Properties | Back 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 Information | Back Directory | [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 |
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