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| CAS No.: | 13676-54-5 |
|---|---|
| Name: | Bismaleimide |
| Molecular Structure: | |
|
|
|
| Formula: | C21H14N2O4 |
| Molecular Weight: | 358.353 |
| Synonyms: | Maleimide,N,N'-(methylenedi-p-phenylene)di- (6CI,7CI,8CI);1,1'-Methylenebis(4-maleimidobenzene);4,4'-(N,N'-Bismaleimido)diphenylmethane;4,4'-Biphenylmethanebismaleimide;4,4'-Bis(maleimido)diphenylmethane;4,4'-Diphenylmethanebismaleimide;4,4'-Methylenedianiline bismaleimide;Bismaleimidodiphenylmethane;Methylenedi-p-phenylene-N,N'-bismaleimide;N,N'-(4,4'-Diphenylmethane)bismaleimide;N,N'-(Methylenedi-4,1-phenylene)bismaleimide;N,N'-Bismaleimido-4,4'-diphenylmethane;p,p'-Dimaleimidodiphenylmethane; |
| EINECS: | 237-163-4 |
| Density: | 1.43 g/cm3 |
| Melting Point: | 156-158 °C(lit.) |
| Boiling Point: | 584.9 °C at 760 mmHg |
| Flash Point: | 278.3 °C |
| Solubility: | Insoluble in water. |
| Appearance: | yellow to brownish fine crystalline powder |
| Hazard Symbols: |
 T
|
| Risk Codes: | 23-36/37/38 |
| Safety: | 26-45-37/39 |
| Transport Information: | UN 2811 6.1/PG 2 |
| PSA: | 74.76000 |
| LogP: | 2.26620 |
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- 108-31-6
maleic anhydride
- 101-77-9
4,4'-diamino diphenyl methane
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With acetic anhydride; acetic acid at 100℃; for 0.25h; Temperature; Microwave irradiation; | 92.1% |
| carboxymethyl-dodecyl-dimethyl-ammonium betaine In ethylbenzene at 70℃; for 8h; Product distribution / selectivity; Heating / reflux; Azeotropic water removal; | 77.6% |
| betaine In toluene at 70℃; for 8h; Product distribution / selectivity; Heating / reflux; Azeotropic water removal; | 75.41% |
- 108-31-6
maleic anhydride
- 2421-28-5
dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With sodium acetate; acetic anhydride; sodium hydrogencarbonate In acetone | 75% |
- 6330-01-4
(Z)-3-{4-[4-((Z)-3-Carboxy-acryloylamino)-benzyl]-phenylcarbamoyl}-acrylic acid
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate In 1-Propyl acetate for 3h; Reflux; | 50% |
| Stage #1: (Z)-3-{4-[4-((Z)-3-Carboxy-acryloylamino)-benzyl]-phenylcarbamoyl}-acrylic acid With sodium acetate In acetone Reflux; Stage #2: With acetic anhydride In acetone for 8h; Reflux; |
- 585-47-7
benzene-1,3-disulfonyl chloride
- 7300-91-6
N-(4-hydroxyphenyl)maleimide
- 63381-38-4
N-(3-hydroxyphenyl)-maleimide
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane |
- 585-47-7
benzene-1,3-disulfonyl chloride
- 63381-38-4
N-(3-hydroxyphenyl)-maleimide
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane |
- 585-47-7
benzene-1,3-disulfonyl chloride
- 7300-91-6
N-(4-hydroxyphenyl)maleimide
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane |
- 108-31-6
maleic anhydride
- 2421-28-5
dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| In acetone |
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C43H44N4O10
A
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N,N-diglycidyl-furfurylamine
B
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| at 110℃; Retro-Diels-Alder reaction; |
- 101-77-9
4,4'-diamino diphenyl methane
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: toluene / 3 h / 20 °C 2: 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate / 1-Propyl acetate / 3 h / Reflux View Scheme | |
| Multi-step reaction with 2 steps 1.1: acetone / 8 h / Inert atmosphere 2.1: sodium acetate / acetone / Reflux 2.2: 8 h / Reflux View Scheme |
A
- 1883-75-6
2,5-bis-(hydroxymethyl)furan
B
- 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide
| Conditions | Yield |
|---|---|
| at 110℃; for 2h; Temperature; |
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Consensus Reports
Specification
The CAS registry number of Bis(4-maleimidophenyl)methane is 13676-54-5. Its EINECS registry number is 237-163-4. The IUPAC name is 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione. In addition, the molecular formula is C21H14N2O4 and the molecular weight is 358.35. It is also called 1,1'-methylenebis(4-maleimidobenzene). What's more, it is a kind of yellow to brownish fine crystalline powder and belongs to the classes of Industrial/Fine Chemicals; Diphenylmethanes (for High-Performance Polymer Research); Functional Materials; N-Substituted Maleimides; N-Substituted Maleimides, Succinimides & Phthalimides; Reagent for High-Performance Polymer Research.
Physical properties about this chemical are: (1)ACD/LogP: 1.95; (2)ACD/LogD (pH 5.5): 1.95; (3)ACD/LogD (pH 7.4): 1.95; (4)ACD/BCF (pH 5.5): 17.88; (5)ACD/BCF (pH 7.4): 17.88; (6)ACD/KOC (pH 5.5): 274.19; (7)ACD/KOC (pH 7.4): 274.19; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 74.76 Å2; (11)Index of Refraction: 1.689; (12)Molar Refractivity: 95.7 cm3; (13)Molar Volume: 250.4 cm3; (14)Polarizability: 37.94 ×10-24cm3; (15)Surface Tension: 69.8 dyne/cm; (16)Density: 1.43 g/cm3; (17)Flash Point: 278.3 °C; (18)Enthalpy of Vaporization: 87.39 kJ/mol; (19)Boiling Point: 584.9 °C at 760 mmHg; (20)Vapour Pressure: 1.15E-13 mmHg at 25°C.
Uses of Bis(4-maleimidophenyl)methane: it can react with 2,6-Di-tert-butyl-4-mercapto-phenol to get 4,4'-bis[3-(3,5-di-t-butyl-4-hydroxyphenylthio)-2,5-dioxopyrrolidin-1-yl]diphenylmethane. This reaction will need reagent triethylamine and solvents toluene and CH2Cl2. The yield is about 48% with ambient temperature.
![Bis(4-maleimidophenyl)methane can react with 2,6-Di-tert-butyl-4-mercapto-phenol to get 4,4'-bis[3-(3,5-di-t-butyl-4-hydroxyphenylthio)-2,5-dioxopyrrolidin-1-yl]diphenylmethane](/UserFilesUpload/Uses of Bis(4-maleimidophenyl)methane.gif)
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. And it is toxic by inhalation. During using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1\C=C/C(=O)N1c2ccc(cc2)Cc3ccc(cc3)N4C(=O)\C=C/C4=O
(2)InChI: InChI=1/C21H14N2O4/c24-18-9-10-19(25)22(18)16-5-1-14(2-6-16)13-15-3-7-17(8-4-15)23-20(26)11-12-21(23)27/h1-12H,13H2
(3)InChIKey: XQUPVDVFXZDTLT-UHFFFAOYAR
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(11), Pg. 109, 1975. | |
| rat | LC50 | inhalation | 350mg/m3/4H (350mg/m3) | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0790-1023S, | |
| rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(11), Pg. 109, 1975. |