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N-Phenylmaleimide

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Name

N-Phenylmaleimide

EINECS 213-382-0
CAS No. 941-69-5 Density 1.329 g/cm3
PSA 37.38000 LogP 1.18100
Solubility Soluble in water (slightly ), methanol, ethanol, and benzene. Melting Point 85-87 °C(lit.)
Formula C10H7NO2 Boiling Point 299.26 °C at 760 mmHg
Molecular Weight 173.171 Flash Point 136.835 °C
Transport Information UN 2811 6.1/PG 3 Appearance yellow crystalline powder or needles
Safety 45-24/25-36/37/39-26 Risk Codes 25-36/37/38-23/24/25
Molecular Structure Molecular Structure of 941-69-5 (N-Phenylmaleimide) Hazard Symbols ToxicT,IrritantXi
Synonyms

Maleimide,N-phenyl- (8CI);1-Phenyl-1H-pyrrole-2,5-dione;1-Phenyl-pyrrole-2,5-dione;Imilex P;Maleanil;Maleimidobenzene;N-Phenylmaleic acid imide;1H-Pyrrole-2,5-dione,1-phenyl-;N-Phenylpyrrole-2,5-dione;NSC8183;Phenylmaleimide;

Article Data 163

N-Phenylmaleimide Synthetic route

555-59-9, 4437-08-5, 37902-58-2

N-phenylmaleamic acid

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%
108-31-6

maleic anhydride

62-53-3

aniline

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%
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

941-69-5

N-phenyl-maleimide

B

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%
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

941-69-5

N-phenyl-maleimide

B

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%
36342-11-7

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

941-69-5

N-phenyl-maleimide

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

3-phenylcarbamoylacrylic acid

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

A

486-86-2

(-)-N-methylcystine

B

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

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

maleic anhydride

538-51-2

benzylidene phenylamine

941-69-5

N-phenyl-maleimide

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

maleic anhydride

2362-79-0

N-(4-chlorobenzylidene)aniline

941-69-5

N-phenyl-maleimide

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

1-phenylpyrrole

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-Phenylmaleimide Chemical Properties

Molecular Structure of N-Phenylmaleimide (CAS NO.941-69-5):

IUPAC Name: 1-Phenylpyrrole-2,5-dione
Molecular Formula: C10H7NO2
Molecular Weight: 173.17 g/mol
Density: 1.329 g/cm3.
Melting Point: 85-87 °C
Boiling Point: 162-163 °C at 12 mm Hg(lit.)
Flash Point: 136.8 °C
Index of Refraction: 1.629
Molar Refractivity: 46.32 cm3
Molar Volume: 130.2 cm3
Surface Tension: 57.4 dyne/cm 
XLogP3: 1.1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 173.047678
MonoIsotopic Mass: 173.047678
Topological Polar Surface Area: 37.4
Heavy Atom Count: 13 
Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C=CC2=O
InChI: InChI=1S/C10H7NO2/c12-9-6-7-10(13)11(9)8-4-2-1-3-5-8/h1-7H
InChIKey: HIDBROSJWZYGSZ-UHFFFAOYSA-N
EINECS: 213-382-0
Product Categories: N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks

N-Phenylmaleimide Uses

 N-Phenylmaleimide (941-69-5) is used as sulfide cross-linking agent in caoutchouc and synthetic rubber. It is also used as heat-resistant modifying agent in the resins of ABS, PVC, and PMMA. N-Phenylmaleimide is used as the  intermediate of resins and is prepared for heat resistant polymers. N-Phenylmaleimide is widely used in coatings, binder, light-sensitive resins medicines, farm chemicals and so on.

N-Phenylmaleimide Toxicity Data With Reference

1.    

skn-rbt 500 mg MLD

    SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
2.    

orl-rat LD50:188 mg/kg

    SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
3.    

ipr-rat LDLo:25 mg/kg

    NCNSA6    National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),22.
4.    

orl-mus LD50:78 mg/kg

    SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
5.    

orl-rbt LDLo:100 mg/kg

    SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)

N-Phenylmaleimide Consensus Reports

Reported in EPA TSCA Inventory.

N-Phenylmaleimide Safety Profile

Hazard Codes: ToxicT, IrritantXi
Risk Statements: 25-36/37/38-23/24/25 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 45-24/25-36/37/39-26 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S24/25:Avoid contact with skin and eyes. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: ON5950000
F: 10-21
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
HS Code: 29251995
Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

N-Phenylmaleimide Specification

 N-Phenylmaleimide (CAS NO.941-69-5) is also named as 5-21-10-00009 (Beilstein Handbook Reference) ; AI3-01186 ; 
BRN 0125098 ; Maleanil ; Maleimidobenzene ; Maleinanil ; N-Fenylimid kyseliny maleinove ; N-Fenylimid kyseliny maleinove [Czech] ; NSC 8183 ; 1H-Pyrrole-2,5-dione, 1-phenyl- ; Maleimide, N-phenyl- . N-Phenylmaleimide (CAS NO.941-69-5) is yellow crystalline powder or needles. It is sparingly water soluble. N-Phenylmaleimide is an imide. 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). 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. Flash point data for N-Phenylmaleimide are not available. It is probably combustible.

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