N-(Ethanol)maleimide supplier

Name
1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE
EINECS
CAS No. 1585-90-6
Article Data28
CAS DataBase
Density 1.395 g/cm³
Solubility
Melting Point 70-71℃
Formula C₆H₇NO₃
Boiling Point 304.5 °C at 760 mmHg
Molecular Weight 141.126
Flash Point 138 °C
Transport Information
Appearance
Safety 26
Risk Codes 22-36
Molecular Structure
Hazard Symbols Xn
Synonyms N-(2-Hydroxyethyl)maleimide;2-Hydroxyethyl maleimide;1-(2-Hydroxyethyl)pyrrole-2,5-dione;Maleimide,N-(2-hydroxyethyl)- (7CI,8CI);
PSA 57.61000
LogP -1.15840

Synthetic route

: 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
In toluene at 110℃; Inert atmosphere;	99%
In toluene at 110℃; for 5h; Inert atmosphere;	28%
In toluene Reflux;

: 32620-90-9
4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With 1,4-dimethoxybezene In xylene at 130℃; for 3.25h; Heating / reflux;	93%
In toluene at 105℃; for 16h;	92%
In toluene at 120℃;	82%

: 108-31-6
maleic anhydride

: 141-43-5
ethanolamine

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With sulfuric acid; copper(II) sulfate; sodium sulfate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h;	88%
Stage #1: maleic anhydride; ethanolamine In acetone at 20℃; for 1h; Stage #2: With sodium acetate; triethylamine; hydroquinone at 115℃; for 2.5h;	30%
In toluene at 80℃; for 2h;	25%

: 1585-79-1
2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl acetate

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water for 72h; Heating;	81%

: 55750-48-6
N-methoxycarbonylmaleimide

: 141-43-5
ethanolamine

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With sodium hydrogencarbonate at 0 - 25℃;	75%
With sodium hydrogencarbonate In water	63%

: C10H11NO4

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
In toluene for 10h; Reflux;	54%

: 1585-93-9
2-[(3-carboxy-1-oxo-2-propenyl)amino]-ethanol

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride at 70℃;	35%
With sulfuric acid at 60℃;

: 15519-86-5
N-(2-Hydroxyethyl)-maleinsaeureamid

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With triethylamine In toluene for 2h; Heating;	14%

: 6719-02-4
2-(1H-pyrrol-1-yl)ethanol

A: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

B: 1186033-58-8
2,3-dihydropyrrolo[2,1-b]oxazol-5(7ah)-one

C: 1186033-59-9
5-hydroxy-1-(2-hydroxyethyl)-1H-pyrrol-2(5H)-one

Conditions

Conditions	Yield
With water; oxygen; 5,15,10,20-tetraphenylporphyrin In tetrachloromethane at 0℃; Irradiation;
With decatungstate(4-); water; oxygen In acetonitrile at 0℃; Irradiation;

...Expand

: 6719-02-4
2-(1H-pyrrol-1-yl)ethanol

: 67-56-1
methanol

A: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

B: 1186033-58-8
2,3-dihydropyrrolo[2,1-b]oxazol-5(7ah)-one

C: 1186033-59-9
5-hydroxy-1-(2-hydroxyethyl)-1H-pyrrol-2(5H)-one

D: 1186033-60-2
1-(2-hydroxyethyl)-5-methoxy-1H-pyrrol-2(5H)-one

Conditions

Conditions	Yield
With water; oxygen; rose bengal at 0℃; Irradiation;

...Expand

: 2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
Heating;

: 2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

A: 98-00-0
(2-furyl)methyl alcohol

B: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
at 100℃; Kinetics; Temperature;

: (3aR,4R,7S,7aS)-2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
In toluene Reflux;
In toluene for 48h; Reflux;

: 110-00-9
furan

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 847757-03-3, 245092-44-8
(+/-)-(3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
In benzene Diels-Alder reaction; Heating;	99%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 104784-61-4
[2-(anthracen-9-yl)ethynyl]trimethylsilane

: 13-(2-hydroxyethyl)-9-((trimethylsilyl)ethynyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione

Conditions

Conditions	Yield
In toluene at 120℃; Diels-Alder Cycloaddition;	97%
In toluene at 120℃;	89%

: 98-00-0
(2-furyl)methyl alcohol

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: C11H13NO5

Conditions

Conditions	Yield
In toluene at 75℃; for 24h; Diels-Alder Cycloaddition;	95%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: C31H31NO2S3

: C37H38N2O5S3

Conditions

Conditions	Yield
With zinc tetraphenylporphyrin In dimethylsulfoxide-d6 at 20℃; for 20h; Irradiation; Inert atmosphere; Sealed tube; stereospecific reaction;	95%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 523-27-3
9,10-Dibromoanthracene

: N-(2-hydroxyethyl)-1,4-dibromodibenzo[e,h]bicyclo[2.2.2]octane-2,3-dicarboximide

Conditions

Conditions	Yield
In toluene at 160℃; for 4h;	94%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 358-23-6
trifluoromethylsulfonic anhydride

: 155863-37-9
2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl trifluoromethanesulfonate

Conditions

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	91%
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 1h;

: 98-00-0
(2-furyl)methyl alcohol

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
In toluene at 75℃; for 12h; Diels-Alder Cycloaddition;	90.09%
In ethyl acetate at 60℃; for 48h; Solvent; Temperature; Diels-Alder Cycloaddition; Inert atmosphere;	81%
In benzene for 20h; Reflux;	62%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 65967-52-4
diketene acetal (3,9-bis(ethylidene)-2,4,8,10-tetraoxaspiro<5,5>undecane)

: 118377-60-9
C23H30N2O10

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In diethyl ether at 20℃; for 2h; Inert atmosphere;	90%

: 98-00-0
(2-furyl)methyl alcohol

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: (3aR,4S,7R,7aS)-rel-3a,4,7,7a-tetrahydro-2-(2-hydroxyethyl)-4-(hydroxymethyl)-4,7-epoxy-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
In toluene at 80℃;	90%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 5070-13-3
bis-(p-nitrophenyl) carbonate

: 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl (4-nitrophenyl)carbonate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	88%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 18063-02-0
2,6-difluorobenzoylchloride

: 1333082-91-9
2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl 2,6-difluorobenzoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	87%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: C23H26N5O3

: C29H33N4O6

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 0.25h; Irradiation; Inert atmosphere;	87%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 621-23-8
1,2,3-trimethoxybenzene

: N-(2-hydroxyethyl)-3-(2,4,6-trimethoxyphenyl)succinimide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 100℃; for 5h;	86%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 98-59-9
p-toluenesulfonyl chloride

: 34321-85-2
N-(2-Tosyloxyethyl)-maleimid

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 72h; Ambient temperature;	85%
With triethylamine In dichloromethane at 0 - 20℃; for 24h;	73%

: 9-anthyrylmethyl 2-bromo-2-methyl propanoate

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: C25H24BrNO5

Conditions

Conditions	Yield
In isopropyl alcohol; toluene for 12h; Reflux;	85%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: tert-butyl 4-(5-(2-methoxy-1,1,3,3-tetramethylisoindolin-5-yl)-2H-tetrazol-2-yl)benzoate

: tert-butyl 4-(5-(2-hydroxyethyl)-3-(2-methoxy-1,1,3,3-tetramethylisoindolin-5-yl)-4,6-dioxo-4,5,6,6a-tetrahydropyrrolo[3,4-c]-pyrazol-1(3aH)-yl)benzoate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 0.25h; Irradiation; Inert atmosphere;	84%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 26307-17-5
2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dienone

: 4-(2-hydroxyethyl)-1,7-dimethyl-8,9-diphenyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5,10-trione

Conditions

Conditions	Yield
In benzene for 6h; Heating;	84%

: 500-22-1
3-pyridinecarboxaldehyde

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 107-97-1
sarcosine

: 2-(2-hydroxyethyl)-5-methyl-4-(pyridin-3-yl)tetrahydropyrrolo-[3,4-c]pyrrole-1,3(2H,3aH)-dione

Conditions

Conditions	Yield
In 1,4-dioxane at 100℃; for 6h; Optical yield = 4 %de;	83%

...Expand

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 32315-10-9
bis(trichloromethyl) carbonate

: 2-maleimidoethyl chloroformiate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 72h; Ambient temperature;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 20769-85-1
2-bromoisobutyric acid bromide

: 653599-62-3
2-bromo-2-methylpropionic acid 2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Cooling with ice;	80%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 42h;	69%

: 124-09-4
1,6-Hexanediamine

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 1297582-69-4
C18H30N4O6

Conditions

Conditions	Yield
In chloroform for 24h; Michael-like addition; Reflux;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 646-19-5
heptane-1,7-diamine

: 1297582-71-8
C19H32N4O6

Conditions

Conditions	Yield
In chloroform for 24h; Michael-like addition; Reflux;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 373-44-4
1,8-diaminooctan

: 1297582-72-9
C20H34N4O6

Conditions

Conditions	Yield
In chloroform for 24h; Michael-like addition; Reflux;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 2912-62-1
α-chlorophenylacetyl chloride

: 1445784-01-9
2-maleimidoethyl 2-chloro-2-phenylacetate

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 15396-00-6
3-(trimethoxysilyl)propyl isocyanate

: C12H20N2O7Si

Conditions

Conditions	Yield
With dibutyltin dilaurate In toluene at 50 - 58℃; Inert atmosphere;	80%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 4-{5-[bis(2-chloro-ethyl)amino]-1-methyl-2-benzimidazolyl}butyric acid hydrochloride

: 1297582-82-1
2-{4-[6-bis(2-chloroethyl)amino-3-methylbenzo[d]imidazol-2-yl]butanoyl}oxyethylmaleimide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24.5h;	79.8%

N-(Ethanol)maleimide Specification

The 1H-Pyrrole-2,5-dione,1-(2-hydroxyethyl)- is an organic compound with the formula C₆H₇NO₃. The IUPAC name of this chemical is 1-(2-Hydroxyethyl)pyrrole-2,5-dione. With the CAS registry number 1585-90-6, it is also named as N-2-Hydroxy-ethymaleimide. The product's category is Pharmacetical. Besides, its molecular weight is 141.12.

Physical properties about 1H-Pyrrole-2,5-dione,1-(2-hydroxyethyl)- are: (1)ACD/LogD (pH 5.5): -0.81; (2)ACD/LogD (pH 7.4): -0.81; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 8.6; (6)ACD/KOC (pH 7.4): 8.6; (7)#H bond acceptors: 4; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 46.61 Å²; (11)Index of Refraction: 1.56; (12)Molar Refractivity: 32.73 cm³; (13)Molar Volume: 101.1 cm³; (14)Polarizability: 12.97×10^-24 cm³; (15)Surface Tension: 60.4 dyne/cm; (16)Density: 1.395 g/cm³; (17)Flash Point: 138 °C; (18)Enthalpy of Vaporization: 63.19 kJ/mol; (19)Boiling Point: 304.5 °C at 760 mmHg; (20)Vapour Pressure: 8.27E-05 mmHg at 25 °C.

Uses of 1H-Pyrrole-2,5-dione,1-(2-hydroxyethyl)-: it can be used to produce 2-Maleimidoethyl chloroformiate. It will need reagent Et₃N and solvent CH₂Cl₂ with reaction time of 72 hours. The yield is about 80%.

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2
(2)InChIKey: AXTADRUCVAUCRS-UHFFFAOYAR
(3)Std. InChI: InChI=1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2
(4)Std. InChIKey: AXTADRUCVAUCRS-UHFFFAOYSA-N

Product Name

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

Synthetic route

N-(Ethanol)maleimide Specification

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