| Identification | Back Directory | [Name]
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE | [CAS]
1585-90-6 | [Synonyms]
HEMI
N-(Ethanol)maleimide
N-Hydroxyethyl MaleiMide
N-hydroxyethylMaleiciMide
1-(2-Hydroxyethyl)maleimide
N-(2-HYDROXYETHYL)MALEIMIDE
N-(2-Hydroxyethyl)MaleiMide 97%
N-(2-Hydroxyethyl)MaleiMide,99%
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione
1H-Pyrrole-2,5-dione,1-(2-hydroxyethyl)-
N-(2-Hydroxyethyl)MaleiMide | [Molecular Formula]
C6H7NO3 | [MDL Number]
MFCD00465266 | [MOL File]
1585-90-6.mol | [Molecular Weight]
141.12 |
| Chemical Properties | Back Directory | [Melting point ]
70-71℃ | [Boiling point ]
130°C/0.005mmHg(lit.) | [density ]
1.395 | [storage temp. ]
2-8°C | [form ]
Powder | [pka]
14.21±0.10(Predicted) | [color ]
white | [InChI]
InChI=1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2 | [InChIKey]
AXTADRUCVAUCRS-UHFFFAOYSA-N | [SMILES]
N1(CCO)C(=O)C=CC1=O | [CAS DataBase Reference]
1585-90-6 |
| Hazard Information | Back Directory | [Description]
1-(2-hydroxymethyl)-1-H-pyrrole-2,5-dione is a synthetic building block for adding an maleimide group with a hydroxyl handle. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. | [Uses]
1-(2-Hydroxy-ethyl)-pyrrole-2,5-dione is a substituted succinimide with antibacterial and cytotoxic activities. | [reaction suitability]
reagent type: cross-linking reagent | [Synthesis]
General procedure for the synthesis of N-(2-hydroxyethyl)maleimide (HEMI) from 3a,4,7,7a-tetrahydro-2-(2'-hydroxyethyl)-4,7-epoxy-1H-isoindole-1,3(2H)-dione (HEMI-A): 0.19 mol (40 g) of HEMI-A was mixed with 227 g of xylene and 0.005 g of methylhydroquinone ( MEHQ, as antioxidant) was mixed. The reaction was heated under nitrogen protection at reflux at 130 °C for 3 h and 15 min to convert HEMI-A to HEMI with a conversion of 98.7% and a reaction yield of about 98.7%. After completion of the reaction, the reactor was cooled to room temperature, the reaction mixture was filtered and the solid product was washed with 15 g of xylene. The washed solid was dried under vacuum to give 25.1 g of HEMI in 93% yield based on HEMI-A. The purity of HEMI was confirmed to be greater than 99% by 1H-NMR analysis. The mother liquor and wash liquor were combined and the total mass was determined to be 230.2 g, which contained 1.17 g of HEMI, which can be recovered or recycled as described above. | [References]
[1] Patent: WO2007/44169, 2007, A1. Location in patent: Page/Page column 10
[2] Dyes and Pigments, 2017, vol. 145, p. 518 - 527
[3] Organic Letters, 2011, vol. 13, # 16, p. 4364 - 4367
[4] Advanced Functional Materials, 2014, vol. 24, # 33, p. 5261 - 5268,8
[5] Journal of Controlled Release, 2018, vol. 285, p. 187 - 199 |
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