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| CAS No.: | 941-69-5 |
|---|---|
| Name: | N-Phenylmaleimide |
| Article Data: | 163 |
| Cas Database | |
| Molecular Structure: | |
|
|
|
| Formula: | C10H7NO2 |
| Molecular Weight: | 173.171 |
| 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; |
| EINECS: | 213-382-0 |
| Density: | 1.329 g/cm3 |
| Melting Point: | 85-87 °C(lit.) |
| Boiling Point: | 299.26 °C at 760 mmHg |
| Flash Point: | 136.835 °C |
| Solubility: | Soluble in water (slightly ), methanol, ethanol, and benzene. |
| Appearance: | yellow crystalline powder or needles |
| Hazard Symbols: |
 T, Xi
|
| Risk Codes: | 25-36/37/38-23/24/25 |
| Safety: | 45-24/25-36/37/39-26 |
| Transport Information: | UN 2811 6.1/PG 3 |
| PSA: | 37.38000 |
| LogP: | 1.18100 |
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- 941712-23-8TETRT-BUTYL5-PHENYL-1,4-DIAZEPANE-1-CARBOXYLATE
- 941716-31-05-(2-phenylethynyl)- 5H-Dibenzo[a,d]cyclohepten-5-ol
- 941716-85-4Benzenesulfonylchloride, 3-(1-methyl-1H-pyrazol-5-yl)-
- 941716-86-51H-Pyrazole,5-(3-isocyanatophenyl)-1-methyl-
- 941717-10-8Cyclopropanecarboxaldehyde, 2-(4-pyridinyl)-
- 941867-91-04-(Benzyloxy)-1-fluoro-2-nitrobenzene
- 94187-96-9Chandramycin (9CI)
- 555-59-9, 4437-08-5, 37902-58-2
N-phenylmaleamic acid
- 941-69-5
N-phenyl-maleimide
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With triethylamine In diethyl ether for 2h; | 85% |
- 37902-58-2
3-phenylcarbamoylacrylic acid
- 941-69-5
N-phenyl-maleimide
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| In toluene at 110℃; under 760.051 Torr; for 8h; | A 83% B 55 mg C 6 mg |
| Conditions | Yield |
|---|---|
| With acetic acid at 100℃; for 1.16667h; | 78% |
| Conditions | Yield |
|---|---|
| With acetic acid at 100℃; for 1.33333h; | 75% |
| Conditions | Yield |
|---|---|
| With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 18h; Inert atmosphere; Irradiation; | 74% |
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Chemistry
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
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.
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) |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
T, 
Xi
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.
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.