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1,1'-(Methylenedi-4,1-phenylene)bismaleimide

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Name

1,1'-(Methylenedi-4,1-phenylene)bismaleimide

EINECS 237-163-4
CAS No. 13676-54-5 Density 1.43 g/cm3
PSA 74.76000 LogP 2.26620
Solubility Insoluble in water. Melting Point 156-158 °C(lit.)
Formula C21H14N2O4 Boiling Point 584.9 °C at 760 mmHg
Molecular Weight 358.353 Flash Point 278.3 °C
Transport Information UN 2811 6.1/PG 2 Appearance yellow to brownish fine crystalline powder
Safety 26-45-37/39 Risk Codes 23-36/37/38
Molecular Structure Molecular Structure of 13676-54-5 (Bismaleimide) Hazard Symbols ToxicT
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;

Article Data 41

1,1'-(Methylenedi-4,1-phenylene)bismaleimide Synthetic route

108-31-6

maleic anhydride

101-77-9

4,4'-diamino diphenyl methane

13676-54-5

1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions
ConditionsYield
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

polyamide carboxylic acid

polyamide carboxylic acid

2421-28-5

dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid

13676-54-5

1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions
ConditionsYield
With sodium acetate; acetic anhydride; sodium hydrogencarbonate In acetone75%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In acetone
1142408-09-0

C43H44N4O10

A

1116147-23-9

N,N-diglycidyl-furfurylamine

B

13676-54-5

1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions
ConditionsYield
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
ConditionsYield
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

C33H30N2O10

A

1883-75-6

2,5-bis-(hydroxymethyl)furan

B

13676-54-5

1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions
ConditionsYield
at 110℃; for 2h; Temperature;

1,1'-(Methylenedi-4,1-phenylene)bismaleimide Consensus Reports

Reported in EPA TSCA Inventory.

1,1'-(Methylenedi-4,1-phenylene)bismaleimide 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

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.

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