Welcome to LookChem.com Sign In|Join Free

CAS

  • or

941-69-5

Post Buying Request

941-69-5 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

941-69-5 Usage

Description

N-Phenylmaleimide is an organic compound that features a maleimide group attached to a phenyl ring. It is known for its ability to act as a cross-linking agent, a dipolarophile, and a plastic modifier, making it a versatile chemical intermediate in various industrial applications.

Uses

Used in Rubber Industry:
N-Phenylmaleimide is used as a cross-linking agent in rubber vulcanization for improving the heat resistance, impact resistance, and hot melt processability of rubber products.
Used in Polymer Production:
N-Phenylmaleimide is used to produce heat-resistant polymers, which are essential for applications requiring high-temperature stability and durability.
Used in Organic Chemistry:
N-Phenylmaleimide serves as a dienophile in the Diels-Alder reaction, a widely used method in organic chemistry for creating six-membered rings. It typically yields crystalline adducts, which are valuable for further chemical synthesis.
Used in 1,3-Cycloaddition Reactions:
N-Phenylmaleimide is utilized as a dipolarophile in 1,3-cycloaddition reactions with nitrones, which is a useful synthetic strategy for the preparation of crystalline adducts of dienes. This application is particularly relevant in the synthesis of complex organic molecules and pharmaceutical compounds.
Used as a Plastic Modifier:
N-Phenylmaleimide is employed as a plastic modifier to enhance the properties of plastics, such as their heat resistance, impact resistance, and processability, making them suitable for a broader range of applications.

Air & Water Reactions

Sparingly water soluble .

Reactivity Profile

N-Phenylmaleimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Fire Hazard

Flash point data for N-Phenylmaleimide are not available. N-Phenylmaleimide is probably combustible.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 941-69-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,4 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 941-69:
(5*9)+(4*4)+(3*1)+(2*6)+(1*9)=85
85 % 10 = 5
So 941-69-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H7NO2/c12-9-6-7-10(13)11(9)8-4-2-1-3-5-8/h1-7H

941-69-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14616)  N-Phenylmaleimide, 98+%   

  • 941-69-5

  • 25g

  • 555.0CNY

  • Detail
  • Alfa Aesar

  • (A14616)  N-Phenylmaleimide, 98+%   

  • 941-69-5

  • 100g

  • 1523.0CNY

  • Detail
  • Alfa Aesar

  • (A14616)  N-Phenylmaleimide, 98+%   

  • 941-69-5

  • 500g

  • 6852.0CNY

  • Detail
  • Aldrich

  • (P27100)  N-Phenylmaleimide  97%

  • 941-69-5

  • P27100-25G

  • 614.25CNY

  • Detail
  • Aldrich

  • (P27100)  N-Phenylmaleimide  97%

  • 941-69-5

  • P27100-100G

  • 1,869.66CNY

  • Detail

941-69-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Phenylmaleimide

1.2 Other means of identification

Product number -
Other names 1-phenylpyrrole-2,5-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:941-69-5 SDS

941-69-5Synthetic route

N-phenylmaleamic acid
555-59-9, 4437-08-5, 37902-58-2

N-phenylmaleamic acid

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With sulfuric acid In dimethyl sulfoxide; toluene Cyclization; Heating;100%
With sodium acetate at 80 - 85℃; for 4h;85%
With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate In 1-Propyl acetate for 3h; Reflux;83%
maleic anhydride
108-31-6

maleic anhydride

aniline
62-53-3

aniline

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
Stage #1: aniline With 2,4-dimethyl-6-tert-butylphenol; triethylamine; phosphoric acid; zinc diacetate In xylene for 0.0833333h;
Stage #2: maleic anhydride In xylene at 140℃; for 6h; Product distribution / selectivity;
98%
With phosphoric acid; 2,4-dimethyl-6-tert-butylphenol; zinc diacetate; silica gel; triethylamine In xylene at 140℃; for 6h; Product distribution / selectivity; Industry scale;98%
Stage #1: maleic anhydride With 2,5-dimethylbenzenesulfonic acid; toluene-4-sulfonic acid In tetrahydrofuran; benzene at 85℃;
Stage #2: aniline In tetrahydrofuran; benzene at 85℃; for 1h; Temperature; Reagent/catalyst; Solvent;
98.75%
7-phenyl-1,7-diaza-bicyclo<2.2.1>heptane-exo-2,3-exo-5,6-tetracarboxylic acid bisphenylimide
21306-38-7, 65391-92-6, 106974-71-4

7-phenyl-1,7-diaza-bicyclo<2.2.1>heptane-exo-2,3-exo-5,6-tetracarboxylic acid bisphenylimide

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

2,5-diphenyl pyrrolo<3,4-c>pyrazole-(2H,5H)-4,6-dione
106958-76-3

2,5-diphenyl pyrrolo<3,4-c>pyrazole-(2H,5H)-4,6-dione

Conditions
ConditionsYield
at 310℃; under 0.1 Torr;A 95%
B 70%
7-phenyl-1,7-diaza-bicyclo<2.2.1>heptane-endo-2,3-exo-5,6-tetracarboxylic acid bisphenylimide
21306-38-7, 65391-92-6, 106974-71-4

7-phenyl-1,7-diaza-bicyclo<2.2.1>heptane-endo-2,3-exo-5,6-tetracarboxylic acid bisphenylimide

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

2,5-diphenyl pyrrolo<3,4-c>pyrazole-(2H,5H)-4,6-dione
106958-76-3

2,5-diphenyl pyrrolo<3,4-c>pyrazole-(2H,5H)-4,6-dione

Conditions
ConditionsYield
at 310℃; under 0.1 Torr;A 95%
B 70%
3-chloro-1-phenylpyrrolidine-2,5-dione
36342-11-7

3-chloro-1-phenylpyrrolidine-2,5-dione

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With triethylamine In diethyl ether for 2h;85%
3-phenylcarbamoylacrylic acid
37902-58-2

3-phenylcarbamoylacrylic acid

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With ammonium peroxodisulfate In 1,4-dioxane; dimethyl sulfoxide at 100℃; for 7h;84%
With sodium acetate; acetic anhydride at 70℃; for 1h;72%
With sodium acetate; acetic anhydride at 100℃; for 0.5h;43%
(3aR,4S,8S,12R,12aS,12bR)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

(3aR,4S,8S,12R,12aS,12bR)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

A

(-)-N-methylcystine
486-86-2

(-)-N-methylcystine

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

C

(3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

(3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

Conditions
ConditionsYield
In toluene at 110℃; under 760.051 Torr; for 8h;A 83%
B 55 mg
C 6 mg
maleic anhydride
108-31-6

maleic anhydride

benzylidene phenylamine
538-51-2

benzylidene phenylamine

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With acetic acid at 100℃; for 1.16667h;78%
maleic anhydride
108-31-6

maleic anhydride

N-(4-chlorobenzylidene)aniline
2362-79-0

N-(4-chlorobenzylidene)aniline

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With acetic acid at 100℃; for 1.33333h;75%
1-phenylpyrrole
635-90-5

1-phenylpyrrole

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 18h; Inert atmosphere; Irradiation;74%
N-phenylmaleisoimidium perchlorate
136163-24-1

N-phenylmaleisoimidium perchlorate

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With piperidine; triethylamine In diethyl ether for 10h;65%
With morpholine; triethylamine In diethyl ether for 10h;65%
malic acid
617-48-1

malic acid

aniline
62-53-3

aniline

A

D,L-2-Hydroxy-N-phenylsuccinimide
20400-73-1

D,L-2-Hydroxy-N-phenylsuccinimide

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
for 0.25h; Condensation; Heating; microwave irradiation;A 62%
B 19%
3-phenylcarbamoylacrylic acid
37902-58-2

3-phenylcarbamoylacrylic acid

acetic anhydride
108-24-7

acetic anhydride

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
Stage #1: 3-phenylcarbamoylacrylic acid; acetic anhydride With sodium acetate at 50℃; for 2h; Inert atmosphere;
Stage #2: With water at 70℃; for 2h; Inert atmosphere;
44%
maleiimide
541-59-3

maleiimide

2-Phenyl-1,3,2-dioxaborinane
4406-77-3

2-Phenyl-1,3,2-dioxaborinane

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With copper diacetate; oxygen; triethylamine; 4 A molecular sieve In dichloromethane at 45℃; for 20h;43%
ethyl (Z)-3-iodopropenoate
31930-36-6

ethyl (Z)-3-iodopropenoate

phenyl isocyanate
103-71-9

phenyl isocyanate

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With triethylamine; 1,2-bis-(diphenylphosphino)ethane; zinc; dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) In acetonitrile at 80℃; for 36h;37%
C21H19NO3
81280-21-9

C21H19NO3

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

1-methoxy-1-methyl-1H-indene
75950-76-4

1-methoxy-1-methyl-1H-indene

(5aS,5bR,8aR,8bS,8cR)-8b-Methoxy-8c-methyl-7-phenyl-5b,8a,8b,8c-tetrahydro-5aH-7-aza-dicyclopenta[a,cd]indene-6,8-dione
81280-24-2, 81339-68-6

(5aS,5bR,8aR,8bS,8cR)-8b-Methoxy-8c-methyl-7-phenyl-5b,8a,8b,8c-tetrahydro-5aH-7-aza-dicyclopenta[a,cd]indene-6,8-dione

(5aS,5bS,8aS,8bS,8cR)-8b-Methoxy-8c-methyl-7-phenyl-5b,8a,8b,8c-tetrahydro-5aH-7-aza-dicyclopenta[a,cd]indene-6,8-dione
81280-24-2, 81339-68-6

(5aS,5bS,8aS,8bS,8cR)-8b-Methoxy-8c-methyl-7-phenyl-5b,8a,8b,8c-tetrahydro-5aH-7-aza-dicyclopenta[a,cd]indene-6,8-dione

Conditions
ConditionsYield
at 80 - 100℃; under 0.08 Torr;A 31%
B 3%
C 33%
D 21%
N-Phenyl-endo-6-methyl-8-ethyl-8-azabicyclo<2.2.2>oct-4-en-7-one-1,2-dicarboximide
56041-56-6, 77519-61-0

N-Phenyl-endo-6-methyl-8-ethyl-8-azabicyclo<2.2.2>oct-4-en-7-one-1,2-dicarboximide

A

1-Ethyl-3-methyl-2-pyridone
77475-04-8

1-Ethyl-3-methyl-2-pyridone

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

N-Phenyl-exo-6-methyl-8-ethyl-8-azabicyclo<2.2.2>oct-4-en-7-one-1,2-dicarboximide
56041-56-6, 77519-61-0

N-Phenyl-exo-6-methyl-8-ethyl-8-azabicyclo<2.2.2>oct-4-en-7-one-1,2-dicarboximide

Conditions
ConditionsYield
In xylene for 42h; Heating;A n/a
B n/a
C 25%
In xylene for 42h; Product distribution; Heating; convertion of endo into exo isomer;A n/a
B n/a
C 25%
(3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

(3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

A

(-)-N-methylcystine
486-86-2

(-)-N-methylcystine

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
In toluene at 110℃; under 760.051 Torr; for 8h;A 24%
B 14 mg
N-phenyl-maleamic acid methyl ester
90278-98-1

N-phenyl-maleamic acid methyl ester

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With water
aniline
62-53-3

aniline

maleic acid
110-16-7

maleic acid

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With 1,4-dioxane; phosphorus pentoxide
endo-4-phenyl-4-aza-10-oxatricyclo<5.2.1.0>dec-8-ene-3,5-dione
67463-35-8

endo-4-phenyl-4-aza-10-oxatricyclo<5.2.1.0>dec-8-ene-3,5-dione

A

furan
110-00-9

furan

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
In chloroform at 43℃; under 750060 Torr; Kinetics; Thermodynamic data; var.temp. and solv: dioxane; Ea and ΔS(excit.);
exo-10-acetyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione
99237-86-2

exo-10-acetyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione

A

N-acetylpyrrole
609-41-6

N-acetylpyrrole

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
In dimethyl sulfoxide at 55.8℃; under 750060 Torr; Kinetics; Thermodynamic data; var.temp. and solv: dioxane; Ea and ΔS(excit.);
1-Phenyl-pyrrole-2,5-dione; compound with GENERIC INORGANIC NEUTRAL COMPONENT

1-Phenyl-pyrrole-2,5-dione; compound with GENERIC INORGANIC NEUTRAL COMPONENT

C24H17NO2

C24H17NO2

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

C24H17NO2*AlCl3

C24H17NO2*AlCl3

Conditions
ConditionsYield
With aluminium trichloride In benzene at 25℃; Equilibrium constant; distribution constant AlCl3 between the imide and its adduct with anthracene was measured;
endo-10-benzoyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione
99295-58-6

endo-10-benzoyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione

A

N-benzoylpyrrole
5145-65-3

N-benzoylpyrrole

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
In chloroform at 30.7℃; under 750060 Torr; Kinetics; Thermodynamic data; var.temp., pressure and solv: CH2Cl2, AcOEt, MeCN, Me2SO, THF, dioxane; Ea and ΔS(excit.);
exo-10-benzoyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione
99237-79-3

exo-10-benzoyl-4-phenyl-4,10-diazatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione

A

N-benzoylpyrrole
5145-65-3

N-benzoylpyrrole

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
In dimethyl sulfoxide at 71.7℃; under 750060 Torr; Kinetics; Thermodynamic data; var.temp. and solv: dioxane; Ea and ΔS(excit.);
N-phenyl-c-3,c-4-bis(2-hydroxyphenyl)-r-1,c-2-cyclobutanedicarboximide
84319-82-4

N-phenyl-c-3,c-4-bis(2-hydroxyphenyl)-r-1,c-2-cyclobutanedicarboximide

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

dihydroxy-stilbene
18221-50-6

dihydroxy-stilbene

Conditions
ConditionsYield
In methanol for 0.5h; Product distribution; Ambient temperature; Irradiation; correlation between photochemical fission and chemical structure;
(4aR,9aS)-1,4,4a,9a-Tetrahydro-1,4-etheno-anthracene

(4aR,9aS)-1,4,4a,9a-Tetrahydro-1,4-etheno-anthracene

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
Kinetics; Thermodynamic data; Ambient temperature; decomposition, also 80 deg C, ΔG(excit.);
2,3,5-Triphenyl-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione
21939-12-8

2,3,5-Triphenyl-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione

A

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

B

C,N-diphenylnitrone
201024-81-9

C,N-diphenylnitrone

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 25℃; Equilibrium constant; various concentrations of LiClO4 (also in the absence of LiClO4);
3,6-epoxy-N-phenyl-1,2,3,6-tetrahydrophthalimide
27742-33-2

3,6-epoxy-N-phenyl-1,2,3,6-tetrahydrophthalimide

A

furan
110-00-9

furan

B

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 25℃; Equilibrium constant; various concentrations of LiClO4 (also in the absence of LiClO4;
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

1,3-diphenylisobenzofuran
5471-63-6

1,3-diphenylisobenzofuran

2,4,9-triphenyl-(3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-epioxido-benzo[f]isoindole-1,3-dione
36213-67-9

2,4,9-triphenyl-(3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-epioxido-benzo[f]isoindole-1,3-dione

Conditions
ConditionsYield
With ethyl acetate for 0.0166667h; Diels-Alder Cycloaddition;100%
In toluene
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

7-Phenyl-2,3,7-triazabicyclo<3.3.0>oct-2-ene-6,8-dione
53114-48-0

7-Phenyl-2,3,7-triazabicyclo<3.3.0>oct-2-ene-6,8-dione

Conditions
ConditionsYield
In diethyl ether for 1h;100%
In diethyl ether for 1h; Ambient temperature;80%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

N-benzylidenephenylglycine methyl ester
153924-62-0

N-benzylidenephenylglycine methyl ester

methyl 2,c-4,7-triphenyl-6,8-dioxo-3,7-diazabicyclo-<3.3.O>octane-r-2-carboxylate
82461-27-6, 113430-23-2

methyl 2,c-4,7-triphenyl-6,8-dioxo-3,7-diazabicyclo-<3.3.O>octane-r-2-carboxylate

Conditions
ConditionsYield
With triethylamine Product distribution; Ambient temperature; effect of solvents, metal salts as catalysts, and time;100%
In perdeuteriopyridine at 110℃; for 1.5h;100%
In toluene for 48h; Heating;86%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

1,2,3,4,5-Pentamethyl-cyclopenta-2,4-dienylamine
85739-52-2

1,2,3,4,5-Pentamethyl-cyclopenta-2,4-dienylamine

(1S,2R,6S,7R,10S)-10-Amino-1,7,8,9,10-pentamethyl-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
114564-30-6

(1S,2R,6S,7R,10S)-10-Amino-1,7,8,9,10-pentamethyl-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In dichloromethane at 22℃; for 3.5h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

5-(acetylamino)-1,2,3,4,5-pentamethylcyclopentadiene
114564-20-4

5-(acetylamino)-1,2,3,4,5-pentamethylcyclopentadiene

N-((1S,2R,6S,7R,10S)-1,7,8,9,10-Pentamethyl-3,5-dioxo-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-en-10-yl)-acetamide
114564-29-3, 125277-86-3

N-((1S,2R,6S,7R,10S)-1,7,8,9,10-Pentamethyl-3,5-dioxo-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-en-10-yl)-acetamide

Conditions
ConditionsYield
In dichloromethane at 22℃; for 3.5h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

N-phenacylpyridinium bromide
16883-69-5

N-phenacylpyridinium bromide

(3aS,4S,9aR,9bR)-4-Benzoyl-2-phenyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione
88121-62-4

(3aS,4S,9aR,9bR)-4-Benzoyl-2-phenyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Conditions
ConditionsYield
With triethylamine In chloroform for 0.166667h; Ambient temperature;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

pyridinium benzoylmethylide
36377-40-9

pyridinium benzoylmethylide

(3aS,4S,9aR,9bR)-4-Benzoyl-2-phenyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione
88121-62-4

(3aS,4S,9aR,9bR)-4-Benzoyl-2-phenyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Conditions
ConditionsYield
In chloroform for 0.166667h; Ambient temperature;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

1-methoxy-1-trimethylsiloxy-1,3,5-hexatriene
107836-10-2

1-methoxy-1-trimethylsiloxy-1,3,5-hexatriene

(1,3-Dioxo-2-phenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-acetic acid methyl ester
107836-00-0

(1,3-Dioxo-2-phenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-acetic acid methyl ester

Conditions
ConditionsYield
In benzene for 1h; Ambient temperature;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

2,3-bis<(trimethyksilyl)methyl>-1,3-butadiene
82167-48-4

2,3-bis<(trimethyksilyl)methyl>-1,3-butadiene

2-phenyl-5,6-di(trimethylsilylmethyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
82167-60-0

2-phenyl-5,6-di(trimethylsilylmethyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With hydroquinone In toluene Heating;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
26234-46-8, 29377-36-4, 56552-68-2

N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 0.0166667h; Diels-Alder Cycloaddition;100%
With 1-hexyl-3-methylimidazolium tetrafluoroborate; K-10 montmorillonite at 20℃; for 0.0833333h; Diels-Alder reaction;99%
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 0.166667h; Diels-Alder reaction; diastereoselective reaction;97%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

C20H18
65879-08-5

C20H18

C30H25NO2
125512-62-1

C30H25NO2

Conditions
ConditionsYield
In benzene at 80℃; for 30h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

((E)-2-Buta-1,3-dienyl)-6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecene

((E)-2-Buta-1,3-dienyl)-6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecene

4-(6,7,9,10,12,13,15,16,18,19-Decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-2-phenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

4-(6,7,9,10,12,13,15,16,18,19-Decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-2-phenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions
ConditionsYield
In benzene at 75 - 80℃; for 22h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

N-phenylmaleimide
83-25-0

N-phenylmaleimide

Conditions
ConditionsYield
With acetic anhydride; zinc In toluene at 40 - 86℃; for 48h; Inert atmosphere; chemoselective reaction;100%
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane; water In toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere;99%
With ammonium formate; acetic acid; palladium on activated charcoal at 110℃; for 0.166667h; Hydrogenation;96%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

1-cyclohexenyl methyl ketone
932-66-1

1-cyclohexenyl methyl ketone

2-phenyl-octahydro-benzo[e]isoindole-1,3,5-trione

2-phenyl-octahydro-benzo[e]isoindole-1,3,5-trione

Conditions
ConditionsYield
With polymer supported 1-silyloxy-1,3-butadiene In dichloromethane at 25℃; for 14h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

ethyl 3-[(dimethylamino)methyl]-1H-indole-2-acetate
252637-04-0

ethyl 3-[(dimethylamino)methyl]-1H-indole-2-acetate

(3aR,4R,10aR)-1,3-Dioxo-2-phenyl-1,2,3,3a,4,5,10,10a-octahydro-pyrrolo[3,4-b]carbazole-4-carboxylic acid ethyl ester

(3aR,4R,10aR)-1,3-Dioxo-2-phenyl-1,2,3,3a,4,5,10,10a-octahydro-pyrrolo[3,4-b]carbazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene for 2h; Addition; elimination; Heating;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(2Z, 4E)-1,3,6-triacetoxyhexa-2,4-diene
153704-91-7

(2Z, 4E)-1,3,6-triacetoxyhexa-2,4-diene

all cis-4-acetoxy-3,6-diacetoxymethylcyclohex-4-ene-1,2-N-phenyldicarboximide

all cis-4-acetoxy-3,6-diacetoxymethylcyclohex-4-ene-1,2-N-phenyldicarboximide

Conditions
ConditionsYield
hydroquinone In toluene for 7.5h; Cycloaddition; Heating;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

tert-butyl-dimethyl-[1-methylene-3-(2-nitro-phenyl)-allyloxy]-silane
287920-04-1

tert-butyl-dimethyl-[1-methylene-3-(2-nitro-phenyl)-allyloxy]-silane

(3aR,4R,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(2-nitro-phenyl)-2-phenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

(3aR,4R,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(2-nitro-phenyl)-2-phenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions
ConditionsYield
In benzene at 20℃; for 72h; Cycloaddition; Diels-Alder reaction;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(E)-1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane

(E)-1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane

(3aR,4S,8aS)-1,3-Dioxo-2-phenyl-4-triethylsilanyl-2,3,3a,4,5,7,8,8a-octahydro-1H-cyclopenta[f]isoindole-6,6-dicarboxylic acid dimethyl ester

(3aR,4S,8aS)-1,3-Dioxo-2-phenyl-4-triethylsilanyl-2,3,3a,4,5,7,8,8a-octahydro-1H-cyclopenta[f]isoindole-6,6-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In toluene at 80℃; for 20h; Diels-Alder reaction;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(R,E)-3-(tert-butyldimethylsiloxy)-1-(4-phenyl-2-oxazolidinon-3-yl)-1,3-butadiene
325479-30-9

(R,E)-3-(tert-butyldimethylsiloxy)-1-(4-phenyl-2-oxazolidinon-3-yl)-1,3-butadiene

(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione
325479-39-8

(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

Conditions
ConditionsYield
In toluene at -45 - 20℃; for 24h; Diels-Alder reaction;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

2-(1,2,3,4,5-pentamethyl-cyclopenta-2,4-dienyl)-4,5-dihydro-oxazole
552290-47-8

2-(1,2,3,4,5-pentamethyl-cyclopenta-2,4-dienyl)-4,5-dihydro-oxazole

(1S,7R)-10-(4,5-Dihydro-oxazol-2-yl)-1,7,8,9,10-pentamethyl-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(1S,7R)-10-(4,5-Dihydro-oxazol-2-yl)-1,7,8,9,10-pentamethyl-4-phenyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In tetrachloromethane at 25℃; Diels-Alder reaction;100%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

dimethyl 2-aminomalonate
53704-09-9

dimethyl 2-aminomalonate

dimethyl rel-(3R,3aR,6aS)-4,6-dioxo-3-[(E)-2-phenylvinyl]-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

dimethyl rel-(3R,3aR,6aS)-4,6-dioxo-3-[(E)-2-phenylvinyl]-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 5h;100%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

dimethyl 2-aminomalonate
53704-09-9

dimethyl 2-aminomalonate

dimethyl rel-(3R,3aR,6aS)-4,6-dioxo-3-[2-phenylethyl]-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

dimethyl rel-(3R,3aR,6aS)-4,6-dioxo-3-[2-phenylethyl]-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

dimethyl 2-aminomalonate
53704-09-9

dimethyl 2-aminomalonate

benzaldehyde
100-52-7

benzaldehyde

dimethyl rel-(3S,3aR,6aS)-4,6-dioxo-3,5-diphenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

dimethyl rel-(3S,3aR,6aS)-4,6-dioxo-3,5-diphenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3.5h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

dimethyl 2-aminomalonate
53704-09-9

dimethyl 2-aminomalonate

acetaldehyde
75-07-0

acetaldehyde

dimethyl rel-(3R,3aR,6aS)-3-methyl-4,6-dioxo-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

dimethyl rel-(3R,3aR,6aS)-3-methyl-4,6-dioxo-5-phenylhexahydropyrrolo[3,4-c]pyrrole-1,1(2H)-dicarboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 5h;100%
(-)-(S)-2-(E)-4-(Z)-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol
868564-65-2

(-)-(S)-2-(E)-4-(Z)-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(+)-(3aR,4S,7S,7aR,SS)-7-(hydroxymethyl)-2,4-diphenyl-5-(p-tolylsulfinyl)-3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione
868564-67-4

(+)-(3aR,4S,7S,7aR,SS)-7-(hydroxymethyl)-2,4-diphenyl-5-(p-tolylsulfinyl)-3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

Conditions
ConditionsYield
In toluene at 20℃; for 72h; Diels-Alder cycloaddition;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

5-Methyl-5-phenyl-1,3-cyclopentadien
72807-73-9

5-Methyl-5-phenyl-1,3-cyclopentadien

C22H19NO2
1016989-18-6

C22H19NO2

Conditions
ConditionsYield
In tetrachloromethane at 25℃; Diels-Alder reaction;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(2-aminoethanethiolato-N,S)bis(1,2-diaminoethane)cobalt(III) perchlorate

(2-aminoethanethiolato-N,S)bis(1,2-diaminoethane)cobalt(III) perchlorate

[(en)2Co(S(CHCON(C6H5)COCH2)CH2CH2NH2)](ClO4)3

[(en)2Co(S(CHCON(C6H5)COCH2)CH2CH2NH2)](ClO4)3

Conditions
ConditionsYield
With H(1+) In perchloric acid aq. HClO4; to the soln. of Co-compd. in aq. HClO4 was added an org. compd.; after 1-2 h the soln. was dild. with H2O; the react. mixt. was absorbed onto an ion-exchange column; washing with aq. HClO4, elution with NaClO4 (pH 2);; Ba(NO3)2 and K2SO4 were added; KClO4 and BaSO4 were removed by fitration; the soln. was condensed by rotoevapn. at 30°C and was filtered; addn. of HClO4, standing overnight at 8°C; recrystn. from HClO4, cooling for 4 h at the same temp.;;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

3-[1'-(tert-butyldimethylsilyloxy)ethyl]-4-[1-methyleneprop-2-enyl]azetidin-2-one
146254-96-8

3-[1'-(tert-butyldimethylsilyloxy)ethyl]-4-[1-methyleneprop-2-enyl]azetidin-2-one

5-{(2S,3S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione
1000700-65-1

5-{(2S,3S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione

Conditions
ConditionsYield
With indium(III) chloride In acetonitrile at 20℃; for 48h; Diels-Alder Reaction;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(S)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopetanecarboxaldehyde
1242461-34-2

(S)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopetanecarboxaldehyde

Conditions
ConditionsYield
With (S)-3-amino-3-phenylpropanoic acid; caesium carbonate In dichloromethane at 20℃; for 48h; Michael Addition; enantioselective reaction;100%
With NH2-Phg-(D-Pro)-Gly-Leu-OH In acetonitrile at 20℃; for 72h; Michael Addition; enantioselective reaction;95%
Stage #1: cyclopentanealdehyde With dmap; tert-butyl (2S,3R)-2-amino-3-hydroxybutanoate; SULFAMIDE In dichloromethane at 23℃; for 0.0333333h; Michael addition;
Stage #2: N-phenyl-maleimide In dichloromethane at 23℃; for 16h; Michael addition; optical yield given as %ee; enantioselective reaction;
93%

941-69-5Downstream Products

941-69-5Relevant articles and documents

-

Richards et al.

, p. 485,486 (1966)

-

Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C-H Activation

Sen, Chiranjit,Sarvaiya, Bhavesh,Sarkar, Souvik,Ghosh, Subhash Chandra

, p. 15287 - 15304 (2020/12/02)

A room-temperature C-H bond functionalization of benzamides has been developed by merging a photocatalyst with a cobalt catalyst for the synthesis of isoindolone spirosuccinimides. The reaction proceeds in aerobic conditions and does not require any sacrificial external oxidants such as Ag(I) or Mn(III) salts. Visible light activates the photocatalyst, and it acts as an electron-transfer reagent and helps in the fundamental organometallic steps by modulating the oxidation state of the cobalt complex. This C-H bond functionalization and spirocyclization showed wide substrate scope and good functional group tolerance. A possible reaction mechanism was proposed from the experimental outcome, showing that C-H bond activation is irreversible and not the rate-determining step.

Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation

Ghosh, Asim Kumar,Samanta, Sadhanendu,Ghosh, Payel,Neogi, Sukanya,Hajra, Alakananda

supporting information, p. 3093 - 3097 (2020/05/08)

Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 941-69-5