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Quality Control of N-(2-Hydroxyethyl)maleimide Purity: 97% SDS Specification

COA

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NMR

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Product Details of N-(2-Hydroxyethyl)maleimide

CAS No. :	1585-90-6
Formula :	C₆H₇NO₃
M.W :	141.12
SMILES Code :	O=C(C=C1)N(CCO)C1=O
MDL No. :	MFCD00465266
InChI Key :	AXTADRUCVAUCRS-UHFFFAOYSA-N
Pubchem ID :	458487

Safety of N-(2-Hydroxyethyl)maleimide

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501

Application In Synthesis of N-(2-Hydroxyethyl)maleimide

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1585-90-6 ]

[ 1585-90-6 ] Synthesis Path-Downstream 1~35

1
[ 1585-90-6 ]
[ 358-23-6 ]
[ 155863-37-9 ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

2
[ 1585-90-6 ]
[ 7143-01-3 ]
[ 155863-36-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	at 105℃; for 3.5h;Inert atmosphere;	To a flame dried round bottom flask 0.5 g (3.6 mmol) of l-(2-hydroxyethyl)-lW- pyrrole-2,5-dione and 0.7 g (4.0 mmol) of methanesulfonic anhydride was added. The flask was evacuated and refilled with nitrogen. The flask was heated to 105C and stirred for 3.5 hr. The reaction was cooled to room temperature and dissolved in ethyl acetate (5 mL). The solution was taken up into a separatory funnel and washed four times with a saturated solution of sodium carbonate (40 mL). The aqueous layers were collected and washed with ethyl acetate (50 mL). The organic layers were combined and dried with MgS04 and concentrated in vacuo. The product was recrystallized from t-butyl methyl ether to yield 43 % (0.347 g, 1.58 mmol) of 2-(2,5-dioxo-2,5-dihydro-lH-pyrrol- l-yl)ethyl methanesulfonate.XH NMR (400 MHz, CD3CI) 6.78 (s, 2H), 4.41 (t, J = 5.23, 2H), 3.90 (t, J = 5.23, 2H), 3.04 (s, 3H)

References: [1]Patent: WO2012/12612,2012,A2 .Location in patent: Page/Page column 37.
[2]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

3
[ 1585-90-6 ]
[ 32315-10-9 ]
2-maleimidoethyl chloroformiate [ No CAS ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

4
[ 15519-86-5 ]
[ 1585-90-6 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

5
[ 1585-90-6 ]
[ 98-59-9 ]
[ 34321-85-2 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

6
[ 1585-90-6 ]
[ 1821-12-1 ]
4-Phenyl-butyric acid 2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl ester [ No CAS ]

References: [1]Archiv der Pharmazie,1998,vol. 331,p. 47 - 53.

7
[ 1585-90-6 ]
[ 305-03-3 ]
4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid 2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2701 - 2708.

9
[ 108-31-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

Yield	Reaction Conditions	Operation in experiment
30%		Maleic anhydride 0.6mmol weighed into three neck round bottom flask, dissolve with 5ml of acetone, 0.66mmol ethanolamine with 5ml of acetone was dissolved by constant pressure funnel was slowly added dropwise three-necked flask, with magnetic stirring. After the reaction at room temperature for 1h , the acetone solvent was removed by rotary evaporation, use 5ml of toluene as a solvent, 0.012g of anhydrous sodium acetate were added to the reaction system, 0.2ml of triethylamine, 0.018 g of hydroquinone, 115 deg.] C was slowly warmed to reflux for 2.5h, tracing the reaction by thin layer chromatography on silica plates.After the reaction was cooled to room temperature, the solvent was removed by rotary evaporation, to obtain a concentrate, the concentrate was subjected to silica gel column chromatography (eluent: VPetroleum ether: VEthyl acetate= 12: 1), and collecting the target fluid, the rotation solvent in vacuo to give the desired product.Yield 30percent.

References: [1]Archiv der Pharmazie,2016,vol. 349,p. 466 - 474.
[2]Patent: CN107162950,2017,A .Location in patent: Paragraph 0091-0093.
[3]Il Farmaco,2002,vol. 57,p. 421 - 426.

10
[ 1585-90-6 ]
[ 20769-85-1 ]
[ 653599-62-3 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 16768 - 16771.
[2]Macromolecules,2004,vol. 37,p. 18 - 26.

11
[ 1585-79-1 ]
[ 1585-90-6 ]

References: [1]Macromolecules,2004,vol. 37,p. 18 - 26.

12
[ 110-00-9 ]
[ 1585-90-6 ]
[ 847757-03-3 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

13
[ 55750-48-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.
[2]Chemistry Letters,2012,vol. 41,p. 313 - 315.

14
(3aS,4aS,8aR,9aR)-5,6,7,8-Tetrachloro-2-(2-hydroxy-ethyl)-3a,4,4a,8a,9,9a-hexahydro-benzo[f]isoindole-1,3-dione [ No CAS ]
[ 1585-90-6 ]
C₂₀H₂₀Cl₄N₂O₆ [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 825 - 827.

15
[ 1585-90-6 ]
endo-3,4,5,6-Tetrachlorobicyclo<4.4.0>deca-2,4-diene-8,9-dicarboxylic acid N-phenylimide [ No CAS ]
C₂₄H₂₀Cl₄N₂O₅ [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 825 - 827.

16
[ 1585-90-6 ]
[ 847757-14-6 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

17
[ 1585-90-6 ]
[ 847757-12-4 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

18
[ 1585-90-6 ]
[ 847757-10-2 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

19
[ 1585-90-6 ]
[ 158745-41-6 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

20
[ 1585-90-6 ]
2-maleimidoethoxy glycinate trifluoroacetic salt [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

21
[ 1585-90-6 ]
1-<2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium methanesulfonate hemihydrate [ No CAS ]