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

Name
Bismaleimide
EINECS 237-163-4
CAS No. 13676-54-5
Article Data41
CAS DataBase
Density 1.43 g/cm³
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
Hazard Symbols T
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;
PSA 74.76000
LogP 2.26620

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

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

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

Conditions	Yield
With sodium acetate; acetic anhydride; sodium hydrogencarbonate In acetone	75%

...Expand

: 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

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

Conditions	Yield
With triethylamine In dichloromethane

...Expand

: 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

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

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

Conditions	Yield
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

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

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

: C33H30N2O10

A: 1883-75-6
2,5-bis-(hydroxymethyl)furan

B: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions

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

: 35675-41-3
C21H18N2O6

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

Conditions

Conditions	Yield
With nickel diacetate; acetic anhydride; triethylamine for 5h; Reflux;	108.35 g

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 29529-99-5
6-dibutylamino-S-triazine-2,4-dithiol

poly(4,4'-bismaleimidediphenylmethane-co-2-di-n-butylamino-4,6-dimercapto-s-triazine): poly(4,4'-bismaleimidediphenylmethane-co-2-di-n-butylamino-4,6-dimercapto-s-triazine)

Conditions

Conditions	Yield
With triethylamine In butanone at 25℃; for 2h;	100%

: 851166-36-4
N-phenyl-4-trifluoromethylbenzenecarbohydrazonoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 1251004-86-0
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3a,6a-dihydro-1-phenyl-3-[4-(trifluoromethyl)phenyl]pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 15424-14-3
N-phenylbenzohydrazonoyl chloride

: 1251004-64-4
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis(3a,6a-dihydro-1,3-diphenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione)

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 40277-63-2
4-methoxy-N'-phenylbenzohydrazonoyl chloride

: 1251004-81-5
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3a,6a-dihydro-3-(4-methoxyphenyl)-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 50656-04-7
4-benzonitrile

: 1251004-76-8
(3aR,6aR,3a'S,6a'S)-4,4'-[methylenebis[(4,1-phenylene)(3a,4,6,6a-tetrahydro-4,6-dioxo-1-phenylpyrrolo[3,4-c]pyrazole-5,3(1H)-diyl)]]bis[benzonitrile]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 25939-01-9
p-toluoyl chloride phenylhydrazone

: 1251004-73-5
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3a,6a-dihydro-3-(4-methylphenyl)-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 25939-02-0
4-fluoro-N'-phenylbenzohydrazonoyl chloride

: 1251004-71-3
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3-(4-fluorophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 25939-12-2
4-bromo-N-phenylbenzohydrazonoyl chloride

: 1251004-67-7
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3-(4-bromophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 35588-49-9
p-(methylthio)benzoyl chloride phenylhydrazone

: 1251004-85-9
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3a,6a-dihydro-3-[4-(methylthio)phenyl]-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 20147-55-1
N-phenyl-p-nitrobenzhydrazonoyl chloride

: 1251004-79-1
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3a,6a-dihydro-3-(4-nitrophenyl)-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 149-30-4
2-thioxo-3H-1,3-benzothiazole

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C28H19N3O4S2

Conditions

Conditions	Yield
With triethylamine In butanone at 25℃; for 2h;	97%

: 38435-47-1
2-bromo N-hydroxybenzimidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C35H22Br2N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	95%

: 36288-37-6
N-hydroxy-4-methylbenzenecarboximidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C37H28N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	95%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 698-16-8
benzohydroximoyl chloride

: C35H24N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	95%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 1011-84-3
4-nitrobenzohydroximoyl chloride

: C35H22N6O10

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	95%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 50656-02-5
4-Acetoxybenzoylchloridphenylhydrazon

: (3aR,6aR,3a'S,6a'S)-4,4'-[methylenebis[(4,1-phenylene)(3a,4,6,6a-tetrahydro-4,6-dioxo-1-phenylpyrrolo[3,4-c]pyrazole-5,3(1H)-diyl)]]bis[phenyl acetate]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	95%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 4185-99-3
N-hydroxyisonicotinimidoyl chloride

: C33H22N6O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	93%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 36590-52-0
N-phenyl-p-chlorobenzohydrazonoyl chloride

: 1251004-66-6
(3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3-(4-chlorophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione]

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	92%

: 1357616-90-0
5-(azidomethyl)-3-(4-(methylthio)phenyl)-1,2,4-oxadiazole

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: (3aS,3a'R,6aR,6a'S)-5,5'-(methylenebis(4,1-phenylene))bis(1-((3-(4-(methylthio)phenyl)-1,2,4-oxadiazol-5-yl)methyl)-1,6a-dihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-dione)

Conditions

Conditions	Yield
In benzene Inert atmosphere; Reflux;	92%

: N′-methyl-N′-(pyridin-2-yl)benzohydrazide

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 1',1'''-(methylenebis(4,1-phenylene))bis(2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3'-pyrrolidine]-2',3,5'-trione)

Conditions

Conditions	Yield
With silver orthophosphate; cobalt(II) diacetate tetrahydrate; sodium pivalate In 1,2-dichloro-ethane at 140℃; for 24h; Inert atmosphere; Sealed tube;	92%

: 35447-75-7
N-hydroxy-2-nitrobenzimidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C35H22N6O10

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

: 29203-60-9
2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C35H20Cl4N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

: 42202-95-9
4-fluoro-N-hydroxybenzimidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C35H22F2N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

: 39502-43-7
2-fluoro-N-hydroxybenzenecarboxymidoyl chloride

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: C35H22F2N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 29568-74-9
2-chloro-N-hydroxybenzimidoyl chloride

: C35H22Cl2N4O6

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

: 13676-54-5
1,1'-(methylenedi-4,1-phenylene)bismaleimide

: 105363-13-1
C9H10ClNO3

: C39H32N4O10

Conditions

Conditions	Yield
With triethylamine In diethyl ether Ambient temperature;	90%

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)	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.

Product Name

Bismaleimide

Synthetic route

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

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

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