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7300-91-6 Usage

Uses

N-(4-Hydroxyphenyl)maleimide

Check Digit Verification of cas no

The CAS Registry Mumber 7300-91-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,3,0 and 0 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 7300-91:
(6*7)+(5*3)+(4*0)+(3*0)+(2*9)+(1*1)=76
76 % 10 = 6
So 7300-91-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H7NO3/c12-8-3-1-7(2-4-8)11-9(13)5-6-10(11)14/h1-6,12H

7300-91-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-hydroxyphenyl)pyrrole-2,5-dione

1.2 Other means of identification

Product number -
Other names 4-hydroxyphenylmaleimide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7300-91-6 SDS

7300-91-6Synthetic route

maleic anhydride
108-31-6

maleic anhydride

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: maleic anhydride; 4-amino-phenol In acetone at 20℃; for 1h;
Stage #2: With sodium acetate; triethylamine; hydroquinone In toluene at 115℃; for 2.5h;
88.5%
Stage #1: maleic anhydride; 4-amino-phenol In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With phosphorus pentoxide; sulfuric acid In N,N-dimethyl-formamide at 70℃; for 2h;
84%
With sulfuric acid; phosphorus pentoxide In N,N-dimethyl-formamide at 70℃; for 2h;56.8%
4'-hydroxymaleanilic acid
143629-26-9, 28173-23-1

4'-hydroxymaleanilic acid

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide In toluene for 6h; Heating;85%
With sodium acetate; acetic anhydride In tetrahydrofuran at 60℃; for 8h;83.3%
With toluene-4-sulfonic acid; N,N-dimethyl-formamide In toluene at 110℃;64%
C11H11NO3

C11H11NO3

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane Reflux;72%
4-(acetoxyphenyl)maleimide
6637-46-3

4-(acetoxyphenyl)maleimide

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid; water63%
N-(4-hydroxy-phenyl)-maleamic acid
28173-23-1, 143629-26-9

N-(4-hydroxy-phenyl)-maleamic acid

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With acetyl chloride; acetone
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;
exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

A

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

B

2-(n-dodecyl)furan
75308-12-2

2-(n-dodecyl)furan

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 50 - 105℃; Reactivity;
4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid; N,N-dimethyl-formamide / toluene / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C
View Scheme
maleic anhydride
108-31-6

maleic anhydride

C21H26N2O2

C21H26N2O2

4-amino-phenol
123-30-8

4-amino-phenol

A

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

B

C29H26N2O6

C29H26N2O6

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene at 20℃; for 2h; Dean-Stark; Cooling with ice;
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

phenyl chloroformate
1885-14-9

phenyl chloroformate

C17H11NO5

C17H11NO5

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;97%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

2-(n-dodecyl)furan
75308-12-2

2-(n-dodecyl)furan

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

Conditions
ConditionsYield
In acetone at 55℃;96%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

C26H17N2O8P

C26H17N2O8P

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 5 - 7℃; Temperature;95.3%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

cinnamoyl chloride
102-92-1

cinnamoyl chloride

3-phenylacrylic acid 4-(2,5-dioxo-2,5-dihydropyrrole-1-yl)-phenyl ester

3-phenylacrylic acid 4-(2,5-dioxo-2,5-dihydropyrrole-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide 0 deg C, 1 h; 25 deg C, 2 h;95.1%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

diphenylolpropane diglycidyl ether
1675-54-3

diphenylolpropane diglycidyl ether

C31H31NO7

C31H31NO7

Conditions
ConditionsYield
With triphenylphosphine In butanone at 130 - 140℃; for 4h;90%
oxalyl dichloride
79-37-8

oxalyl dichloride

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

bis(4maleimidophenyl)oxalate

bis(4maleimidophenyl)oxalate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0℃; for 2h;90%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

aniline
62-53-3

aniline

N-(3-phenylazo-4-hydroxyphenyl)maleimide
1252759-89-9

N-(3-phenylazo-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
85%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

4-amino-phenol
123-30-8

4-amino-phenol

N-(3-(4-hydroxyphenylazo)-4-hydroxyphenyl)maleimide
1252759-90-2

N-(3-(4-hydroxyphenylazo)-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
81%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

epichlorohydrin
106-89-8

epichlorohydrin

4-(N-maleimido)phenyl glycidyl ether
70657-11-3

4-(N-maleimido)phenyl glycidyl ether

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 48h;80%
With benzyltrimethylammonium chloride at 60℃; for 24h; Inert atmosphere;75%
With benzyltrimethylammonium chloride at 60℃; for 24h; Inert atmosphere;55%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

p-toluidine
106-49-0

p-toluidine

N-(3-(4-methylphenylazo)-4-hydroxyphenyl)maleimide
1252759-91-3

N-(3-(4-methylphenylazo)-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
80%
(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester

(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester
658054-31-0

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 23℃; for 16h;79%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

N-(2-pyridyl)indole
3419-91-8

N-(2-pyridyl)indole

1-(4-hydroxyphenyl)-3-(1-(pyridin-2-yl)-1H-indol-2-yl)pyrrolidine-2,5-dione

1-(4-hydroxyphenyl)-3-(1-(pyridin-2-yl)-1H-indol-2-yl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
With dimanganese decacarbonyl In ethyl acetate at 120℃; for 12h;78%
maleic anhydride
108-31-6

maleic anhydride

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: maleic anhydride; 4-amino-phenol In acetone at 20℃; for 1h;
Stage #2: With sodium acetate; triethylamine; hydroquinone In toluene at 115℃; for 2.5h;
88.5%
Stage #1: maleic anhydride; 4-amino-phenol In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With phosphorus pentoxide; sulfuric acid In N,N-dimethyl-formamide at 70℃; for 2h;
84%
With sulfuric acid; phosphorus pentoxide In N,N-dimethyl-formamide at 70℃; for 2h;56.8%
4'-hydroxymaleanilic acid
143629-26-9, 28173-23-1

4'-hydroxymaleanilic acid

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide In toluene for 6h; Heating;85%
With sodium acetate; acetic anhydride In tetrahydrofuran at 60℃; for 8h;83.3%
With toluene-4-sulfonic acid; N,N-dimethyl-formamide In toluene at 110℃;64%
C11H11NO3

C11H11NO3

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane Reflux;72%
4-(acetoxyphenyl)maleimide
6637-46-3

4-(acetoxyphenyl)maleimide

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid; water63%
N-(4-hydroxy-phenyl)-maleamic acid
28173-23-1, 143629-26-9

N-(4-hydroxy-phenyl)-maleamic acid

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
With acetyl chloride; acetone
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;
exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

A

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

B

2-(n-dodecyl)furan
75308-12-2

2-(n-dodecyl)furan

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 50 - 105℃; Reactivity;
4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid; N,N-dimethyl-formamide / toluene / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: acetone / 2 h / 20 °C
2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C
View Scheme
maleic anhydride
108-31-6

maleic anhydride

C21H26N2O2

C21H26N2O2

4-amino-phenol
123-30-8

4-amino-phenol

A

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

B

C29H26N2O6

C29H26N2O6

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene at 20℃; for 2h; Dean-Stark; Cooling with ice;
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

phenyl chloroformate
1885-14-9

phenyl chloroformate

C17H11NO5

C17H11NO5

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;97%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

2-(n-dodecyl)furan
75308-12-2

2-(n-dodecyl)furan

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

Conditions
ConditionsYield
In acetone at 55℃;96%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

C26H17N2O8P

C26H17N2O8P

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 5 - 7℃; Temperature;95.3%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

cinnamoyl chloride
102-92-1

cinnamoyl chloride

3-phenylacrylic acid 4-(2,5-dioxo-2,5-dihydropyrrole-1-yl)-phenyl ester

3-phenylacrylic acid 4-(2,5-dioxo-2,5-dihydropyrrole-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide 0 deg C, 1 h; 25 deg C, 2 h;95.1%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

diphenylolpropane diglycidyl ether
1675-54-3

diphenylolpropane diglycidyl ether

C31H31NO7

C31H31NO7

Conditions
ConditionsYield
With triphenylphosphine In butanone at 130 - 140℃; for 4h;90%
oxalyl dichloride
79-37-8

oxalyl dichloride

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

bis(4maleimidophenyl)oxalate

bis(4maleimidophenyl)oxalate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0℃; for 2h;90%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

aniline
62-53-3

aniline

N-(3-phenylazo-4-hydroxyphenyl)maleimide
1252759-89-9

N-(3-phenylazo-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
85%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

4-amino-phenol
123-30-8

4-amino-phenol

N-(3-(4-hydroxyphenylazo)-4-hydroxyphenyl)maleimide
1252759-90-2

N-(3-(4-hydroxyphenylazo)-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
81%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

epichlorohydrin
106-89-8

epichlorohydrin

4-(N-maleimido)phenyl glycidyl ether
70657-11-3

4-(N-maleimido)phenyl glycidyl ether

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 48h;80%
With benzyltrimethylammonium chloride at 60℃; for 24h; Inert atmosphere;75%
With benzyltrimethylammonium chloride at 60℃; for 24h; Inert atmosphere;55%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

p-toluidine
106-49-0

p-toluidine

N-(3-(4-methylphenylazo)-4-hydroxyphenyl)maleimide
1252759-91-3

N-(3-(4-methylphenylazo)-4-hydroxyphenyl)maleimide

Conditions
ConditionsYield
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: N-(4-hydroxyphenyl)maleimide With sodium hydroxide In water at 0 - 5℃; for 0.166667h;
80%
(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester

(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester
658054-31-0

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 23℃; for 16h;79%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

N-(2-pyridyl)indole
3419-91-8

N-(2-pyridyl)indole

1-(4-hydroxyphenyl)-3-(1-(pyridin-2-yl)-1H-indol-2-yl)pyrrolidine-2,5-dione

1-(4-hydroxyphenyl)-3-(1-(pyridin-2-yl)-1H-indol-2-yl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
With dimanganese decacarbonyl In ethyl acetate at 120℃; for 12h;78%
formaldehyd
50-00-0

formaldehyd

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

bicyclo[4.2.0]octa-1,3,5-trien-4-amine
55716-66-0

bicyclo[4.2.0]octa-1,3,5-trien-4-amine

N-(3-(benzocyclobutane-4-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)maleimide
1417577-58-2

N-(3-(benzocyclobutane-4-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)maleimide

Conditions
ConditionsYield
In 1,4-dioxane for 12h; Reflux;76%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

1-<2-(p-Chlorophenyl)-3-indolylmethylene>thiosemicarbazide
125471-31-0

1-<2-(p-Chlorophenyl)-3-indolylmethylene>thiosemicarbazide

2-(2-{[2-(4-chlorophenyl)-1H-indol-3-ylmethylene]hydrazono}-4-oxothiazolidin-5-yl)-N-(4-hydroxyphenyl)acetamide

2-(2-{[2-(4-chlorophenyl)-1H-indol-3-ylmethylene]hydrazono}-4-oxothiazolidin-5-yl)-N-(4-hydroxyphenyl)acetamide

Conditions
ConditionsYield
With sodium acetate; acetic acid Reflux;76%
formaldehyd
50-00-0

formaldehyd

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

1-(3-(furan-2-ylmethyl)-3,4-dihydro-2Hbenzo[e][1,3]oxazin-6-yl)-1H-pyrrole-2,5-dione

1-(3-(furan-2-ylmethyl)-3,4-dihydro-2Hbenzo[e][1,3]oxazin-6-yl)-1H-pyrrole-2,5-dione

Conditions
ConditionsYield
In toluene at 100℃; for 6h; Temperature;75.7%
In toluene at 100℃; for 3h;71%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

(S)-methyl 2-acetamido-3-(1-(pyridin-2-yl)-1H-indol-3-yl)propanoate

(S)-methyl 2-acetamido-3-(1-(pyridin-2-yl)-1H-indol-3-yl)propanoate

(S)-methyl 2-acetamido-3-(2-(1-(4-hydroxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1-(pyridin-2-yl)-1H-indol-3-yl)propanoate

(S)-methyl 2-acetamido-3-(2-(1-(4-hydroxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1-(pyridin-2-yl)-1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver(l) oxide In acetonitrile at 80℃; for 2h; Inert atmosphere;72%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

5'-(4-hydroxyphenyl)-2'-phenylspiro[(3H)indol-3,3'(3'aH)[2H]pyrrolo[3,4-d]isoxazole]-2,4',6'-(1H,5'H,6'aH)trione

5'-(4-hydroxyphenyl)-2'-phenylspiro[(3H)indol-3,3'(3'aH)[2H]pyrrolo[3,4-d]isoxazole]-2,4',6'-(1H,5'H,6'aH)trione

Conditions
ConditionsYield
In acetonitrile Inert atmosphere; Reflux; diastereoselective reaction;70%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

(2-phenyl-1H-indol-3-yl)-methylenethiosemicarbazone
125471-32-1

(2-phenyl-1H-indol-3-yl)-methylenethiosemicarbazone

N-(4-hydroxyphenyl)-2-{4-oxo-2-[(2-phenyl-1H-indol-3-ylmethylene)hydrazono]thiazolidin-5-yl}acetamide

N-(4-hydroxyphenyl)-2-{4-oxo-2-[(2-phenyl-1H-indol-3-ylmethylene)hydrazono]thiazolidin-5-yl}acetamide

Conditions
ConditionsYield
With sodium acetate; acetic acid Reflux;68%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

Hexamethylene diisocyanate
822-06-0

Hexamethylene diisocyanate

{6-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenoxycarbonylamino]-hexyl}-carbamic acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

{6-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenoxycarbonylamino]-hexyl}-carbamic acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In toluene for 13h; Heating;67%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

octaperfluorocyclopentene
559-40-0

octaperfluorocyclopentene

C25H12F6N2O6

C25H12F6N2O6

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 50℃; for 3h;61%
(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-8-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-4-yl ester
658054-22-9

(4S,7R,8S,9S,13Z,16S)-chloroformic acid-7-allyl-8-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-4-yl ester

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-8-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-4-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester
658054-23-0

(4S,7R,8S,9S,13Z,16S)-carbonic acid 7-allyl-8-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-4-yl ester 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 23℃; for 16h;59%
furan
110-00-9

furan

N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

2-(4-hydroxyphenyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

2-(4-hydroxyphenyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

Conditions
ConditionsYield
In acetone at -35 - 75℃; for 1h;57%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

((Z)-2-But-1-enyl)-1H-pyrrole

((Z)-2-But-1-enyl)-1H-pyrrole

4α-ethyl-2-(4-hydroxyphenyl)-3aα,4β,5,8bα-tetrahydro-2H,6H-pyrrolo[3,4-e]indole-1,3-dione

4α-ethyl-2-(4-hydroxyphenyl)-3aα,4β,5,8bα-tetrahydro-2H,6H-pyrrolo[3,4-e]indole-1,3-dione

Conditions
ConditionsYield
In toluene for 24h; Diels-Alder reaction; Reflux;54%
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

2-(4-hydroxyphenyl)-5-methyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione

2-(4-hydroxyphenyl)-5-methyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione

Conditions
ConditionsYield
With alizarin red S sensitized TiO2; air In acetonitrile at 30℃; for 20h; Irradiation;54%
With cadmium sulphide In neat (no solvent) at 20℃; for 36h; Irradiation;90 %Chromat.
N-(4-hydroxyphenyl)maleimide
7300-91-6

N-(4-hydroxyphenyl)maleimide

5-fluoro-2-methoxybenzoic acid
394-04-7

5-fluoro-2-methoxybenzoic acid

C17H14FNO4

C17H14FNO4

Conditions
ConditionsYield
With sodium dihydrogenphosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; water at 85℃; for 16h; Green chemistry; chemoselective reaction;50%

7300-91-6Relevant academic research and scientific papers

Optimal synthetic design of second-order nonlinear optical material with good temporal stability

Choi,Song,Jahng,Kim

, p. 17 - 26 (1996)

Second-order nonlinear optical copolymers containing p-hydroxyphenyl maleimide or 4-cinnamoyloxy-phenylmaleimide as a comonomer were newly synthesized. For improving the temporal stability, we adopted the crosslink reaction thermally and photochemically. Second-order nonlinear optical properties of the poled/cured films were investigated in terms of the second harmonic generation (SHG) and linear electro-optic (EO) coefficient measurement. SHG coefficient, d33 was found to be 14 pm/V at the fundamental wavelength of 1064 nm and EO coefficient, r33 was found to be 25-30 pm/V at 633 nm wavelength in two different crosslinked structures. To prevent the orientational relaxation of poled polymer, thermal crosslink reaction was induced using diisocyanate as a crosslinker between the side chains themselves. Another photo-crosslink was induced exposing the film at 257 nm wavelength during poling. Temporal stabilities of second-order NLO coefficients of crosslinked polymer systems were proved much better than that of guest-host system or other side chain polymers.

Comment on: Synthesis of new azo compounds based on N-(4-Hydroxyphenyl)maleimide and N-(4-Methylphenyl)maleimide. Molecules 2010, 15, 7498–7508

Morrison, John J.,Brandt, Viktoria K.,Yeates, Stephen G.

, (2019)

The synthesis of (E)-phenylazo-3-N-(4-hydroxyphenyl)maleimide (1) using a procedure previously reported in Molecules is deemed to be erroneous. A detailed re-investigation of the earlier work suggests that the spectral data for key intermediates and the final product, (1), was mis-assigned. We conclude that compound (1) was not synthesized, but rather an unusual ring opening reaction of the maleimide unit of the starting material, N-(4-hydroxyphenyl)maleimide (2) leading to the generation of (Z)-4-((4-hydroxyphenyl)amino)-4-oxobut-2-enoic acid, (3) was observed instead. Examination of the original experimental data reveals systematic errors in the reporting of all of the combustion microanalytical data. Overall, the present investigation suggests that errors in the interpretation of spectral data, falsification of analytical data and selective editing of experimental results raise questions over the veracity of the work presented in the original paper.

Application of maleimide compound as chitin synthase inhibitor

-

Paragraph 0120-0123; 0136-0139, (2020/07/12)

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

New phosphorus- and nitrogen-containing poly(methyl methacrylate)-based copolymer: Enhanced flame retardancy and thermal stability

Shi, Xingxing,Jiang, Saihua,Xiao, Liang

, p. 333 - 342 (2019/06/17)

Pure poly(methyl methacrylate) (PMMA) always exhibits high flammability and low thermal stability. To address that, a novel reactive comonomer containing phosphorus and nitrogen elements, 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) phenyl diethylphosphoramidate (PDM), was successfully synthesized and then introduced into PMMA matrix through emulsion copolymerization method. The structure of PDM and as-obtained poly(MMA-co-PDM) copolymers was characterized using Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance spectroscopy (1H NMR) and 31P NMR. From thermal gravimetric analysis and microscale combustion calorimeter, the poly(MMA-co-PDM) copolymers exhibit significantly enhanced flame retardancy and thermal stability, such as the higher degradation temperatures, and decreased peak heat release rate (maximally by 24.1%) and total heat release (maximally by 22.1%). The glass transition temperature (Tg) values of poly(MMA-co-PDM) copolymers obtained by differential scanning calorimetry slightly decrease as the raising flexibility of polymer chain. The char residue analysis by scanning electron microscopy and FT-IR demonstrates that the incorporation of PDM can catalyze the charring of copolymers in condensed phase and form an excellent thermal stability char residue with aromatic structure, further preventing the inner substrate from further combustion. The detailed mechanism was proposed.

Monomer compound and preparation method thereof, and copolymer, preparation method and applications thereof

-

Paragraph 0085-0087; 0090; 0091; 0115; 0117; 0120; 0121, (2020/04/17)

The invention relates to the technical field of polymer oil displacement, and discloses a monomer compound and a preparation method thereof, and a copolymer, a preparation method and applications thereof. The monomer compound provided by the invention has a structure represented by a formula (1), is a temperature-resistant and salt-resistant functional monomer, can improve the tackifying property,the temperature resistance and the salt resistance of a copolymer after being introduced into the copolymer, and can make the copolymer have a certain surface activity so as to be well applied to theoil extraction process of an oil field.

A Photochemical Ligation System Enabling Solid-Phase Chemiluminescence Read-Out

Delafresnaye, Laura,Schmitt, Christian W.,Barner, Leonie,Barner-Kowollik, Christopher

supporting information, p. 12538 - 12544 (2019/07/15)

The peroxyoxalate chemiluminescence (PO-CL) reaction is among the most powerful and versatile techniques for the detection of hydrogen peroxide (H2O2) and has been employed in various biological and chemical applications over the past 50 years. However, its two-component nature (peroxyoxalate and fluorophore) limits its use. This contribution introduces an innovative and versatile photochemical platform technology for the synthesis of inherently fluorescent PO probes by exploiting the nitrile imine-mediated tetrazole-ene cycloaddition (NITEC) reaction. In the presence of hydrogen peroxide, the pioneered “2-in-1” molecule emits either yellow or blue light, depending on tetrazole (Tz) structure. Even in the absence of base, the emitted light remains visible and H2O2 could be detected in the nanomolar range. Critically, the PO-Tz can be readily incorporated into polymeric materials. As a first application of this promising material, a tailor-made PO-Tz is grafted on poly(divinylbenzene) (PDVB) particles to enable solid-phase chemiluminescence on microspheres.

Novel AB-type benzoxazine monomer and preparation method thereof

-

Paragraph 0029; 0030, (2019/06/07)

The invention belongs to the technical field of high-performance thermosetting resin, and discloses a novel AB-type benzoxazine monomer and a preparation method thereof. The preparation method comprises the following steps: firstly, synthesizing 4-maleimide phenol by using maleic anhydride and p-aminophenol as raw materials; and then synthesizing the AB-type benzoxazine monomer by using the 4-maleimide phenol, 2-furylamine and paraformaldehyde as raw materials. A melting point of the AB-type benzoxazine monomer is 123 DEG C; after the monomer is molten, a Diels-Alder reaction can be performedbetween a maleimide group and a furan group which are contained in the monomer; firstly, main chain benzoxazine is produced, and then benzoxazine ring opening and ring curing occur by further warming;a curing peak temperature is 213.85 DEG C; and such unique mechanism enables the resin to have good thermal performance. After the monomer is cured, a resin material has a residual carbon rate of 57%at a temperature of 800 DEG C, Td5 of 357 DEG C and Td10 of 401 DEG C. The resin material obtained by the AB-type benzoxazine monomer disclosed by the invention has excellent thermal and mechanical properties and excellent machinability, and is low in production cost and suitable for scale production.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

Hosseini-Sarvari, Mona,Koohgard, Mehdi,Firoozi, Somayeh,Mohajeri, Afshan,Tavakolian, Hosein

supporting information, p. 6880 - 6888 (2018/05/04)

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi

supporting information, p. 5540 - 5549 (2019/01/03)

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Composition, cured product and laminate

-

Paragraph 0181; 0182; 0183; 0190; 0191, (2019/04/26)

The present invention addresses the problem of providing a composition that has excellent heat resistance and excellent adhesiveness. The present invention also addresses the problem of providing: a cured product which is obtained by curing this composition; and a laminate which contains this cured product. The present invention also addresses the problem of providing a heat-resistant material, a heat-resistant member, an electronic material and an electronic member, each of which contains this composition. The above-mentioned problems are solved by providing a composition that contains: a (meth)allyl group-containing maleimide compound which is characterized by having a structure that has one or more benzene rings and by having one or more groups each having a (meth)allyl group and one or more groups each having a maleimide group; and a hydroxyl group-containing maleimide compound which is characterized by having a structure that has one or more benzene rings and by having one or more groups each having a hydroxyl group and one or more maleimide groups.

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