1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE

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CAS:1585-90-6
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CAS:1585-90-6
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  • $0.00 / 25g
  • 2025-06-07
  • CAS:1585-90-6
  • Min. Order: 25g
  • Purity: >98.00%
  • Supply Ability: 25g
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE Basic information
Product Name:1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE
Synonyms:1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE;N-(2-HYDROXYETHYL)MALEIMIDE;N-(2-Hydroxyethyl)MaleiMide;N-(2-Hydroxyethyl)MaleiMide 97%;1-(2-Hydroxyethyl)maleimide;N-(Ethanol)maleimide;N-(2-Hydroxyethyl)MaleiMide,99%;1H-Pyrrole-2,5-dione,1-(2-hydroxyethyl)-
CAS:1585-90-6
MF:C6H7NO3
MW:141.12
EINECS:
Product Categories:Heterocycle-other series;Achiral Nitrogen;pharmacetical;organic amide
Mol File:1585-90-6.mol
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE Structure
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE Chemical Properties
Melting point 66-67 °C (lit.) 67-74 °C
Boiling point 130°C/0.005mmHg(lit.)
density 1.395
storage temp. 2-8°C
pka14.21±0.10(Predicted)
form Powder
color white
InChIInChI=1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2
InChIKeyAXTADRUCVAUCRS-UHFFFAOYSA-N
SMILESN1(CCO)C(=O)C=CC1=O
CAS DataBase Reference1585-90-6
Safety Information
Hazard Codes Xn
Risk Statements 22-36
Safety Statements 26
WGK Germany 3
HS Code 2925.19.9100
MSDS Information
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE Usage And Synthesis
Description1-(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.
Uses1-(2-Hydroxy-ethyl)-pyrrole-2,5-dione is a substituted succinimide with antibacterial and cytotoxic activities.
reaction suitabilityreagent type: cross-linking reagent
Synthesis
3A,4,7,7A-TETRAHYDRO-2-(2'-HYDROXYETHYL)-4,7-EPOXY-1H-ISOINDOLE-1,3(2H)-DIONE

32620-90-9

1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE

1585-90-6

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
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE Preparation Products And Raw materials
Raw materials3A,4,7,7A-TETRAHYDRO-2-(2'-HYDROXYETHYL)-4,7-EPOXY-1H-ISOINDOLE-1,3(2H)-DIONE-->Maleic anhydride-->Monoethanolamine-->Xylene-->1,4-Dimethoxybenzene
Tag:1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE(1585-90-6) Related Product Information
Maleimide Mal-amido-PEG1-acid Mal-PEG1-t-butyl ester Mal-PEG1-Val-Cit-PAB-PNP Mal-PEG1-acid 2,5-Dioxopyrrolidin-1-yl 3-(2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)propanoate N-Succinimidyl maleimidoacetate DACM 2-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-PROPIONIC ACID 1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE MESS 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-phenylpropanoic acid 1-(2-METHOXY-ETHYL)-PYRROLE-2,5-DIONE 3-MALEIMIDO-4-METHYL-6,7-METHYLENEDIOXYCOUMARIN 2-MALEIMIDOETHYL MESYLATE 1,11-BIS-MALEIMIDOTETRAETHYLENEGLYCOL 2-Maleimido acetic acid 1,8-BIS-MALEIMIDOTRIETHYLENEGLYCOL

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