N,N'-1,3-Phenylene bismaleimide supplier

Name
N,N'-1,3-Phenylene bismaleimide
EINECS 221-112-8
CAS No. 3006-93-7
Article Data14
CAS DataBase
Density 1.567 g/cm³
Solubility negligible soluble in water
Melting Point 198-201 °C(lit.)
Formula C₁₄H₈N₂O₄
Boiling Point 499.3 °C at 760 mmHg
Molecular Weight 268.229
Flash Point 250.7 °C
Transport Information UN 2811 6.1/PG 2
Appearance yellow crystalline powder
Safety 27-28-36/37/39-45-38-28A
Risk Codes 23/24/25-36/37/38-26-22
Molecular Structure
Hazard Symbols Xi, T, T+
Synonyms N,N-m-phenylenedimaleimide;Maleimide,N,N'-m-phenylenedi- (6CI,7CI,8CI);1,1'-(1,3-Phenylene)bis[1H-pyrrole-2,5-dione];1,3-Bismaleimidobenzene;1,3-Dimaleimidobenzene;1,3-Phenylenebismaleimide;Actor PBM-R;BMI 3000;BMI-MP;Burnock PM;HVA 2;N,N'-1,3-Phenylenebismaleimide;N,N'-1,3-Phenylenedimaleimide;N,N'-m-Phenylenebis[maleimide];N,N'-m-Phenylenedimaleimide;NSC 19639;PMI;SR 525;SR 525A;Sanfel BM-G;Sumifine BM;Sumilizer BM;Vanax MBM;Vulkanox PM;Vulnoc PM;Vulnoc PM-P;m-Dimaleimidobenzene;m-Phenylenebismaleimide;m-Phenylenedimaleimide;
PSA 74.76000
LogP 0.67540

Synthetic route

: 108-31-6
maleic anhydride

: 16674-78-5
magnesium(II) acetate tetrahydrate

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

Conditions

Conditions	Yield
With acetic anhydride In water; acetone	84%

N,N'-m-phenylene-bis-malamic acid: N,N'-m-phenylene-bis-malamic acid

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride

: 108-31-6
maleic anhydride

: 108-45-2
m-phenylenediamine

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

Conditions

Conditions	Yield
In ethyl acetate; toluene at 60℃; for 5h; Time; Temperature;

: S01819

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

Conditions

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid Reflux;

: 60698-27-3
5-p-tolyloxy-furan-2-carboxylic acid

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 113452-03-2
C36H24N2O6

Conditions

Conditions	Yield
With trifluoroacetic acid In chloroform-d1 at 100℃;	96%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 1-benzyl-3-((2,2,2-trifluoroethyl)imino)indolin-2-one

: 5',5'''-(1,3-phenylene)bis(1-benzyl-3'-(trifluoromethyl)-2',3',3a',6a'-tetrahydro-4'H-spiro[indoline-3,1'-pyrrolo[3,4-c]pyrrole]-2,4',6'(5'H)-trione)

Conditions

Conditions	Yield
With tetrahexylammonium bromide; sodium carbonate In dichloromethane at 20℃; for 0.133333h; diastereoselective reaction;	92%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

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

: 1',1'''-(1,3-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;	84%

: 107-86-8
3,3-dimethyl acrylaldehyde

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 2,2′-(1,3-phenylene)bis(5-methylisoindoline-1,3-dione)

Conditions

Conditions	Yield
With benzoic acid; L-proline In toluene at 80℃; for 15h;	83%

: 57796-76-6
2-vinyloxy-1,3-butadiene

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 88848-43-5
1,3-bis-(4-vinyloxy-Δ4-tetrahydrophthalimido)benzene

Conditions

Conditions	Yield
at 100℃; for 0.5h;	76.1%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 80447-71-8
phenylhydrazone of ethyl ester of glyoxalic acid

: diethyl 5,5'-(1,3-phenylene)(3aS,3a'S,6aS,6a'S)-bis(4,6-dioxo-1-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylate)

Conditions

Conditions	Yield
With copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 2h;	76%

: 886-65-7, 538-81-8
trans,trans-1,4-Diphenyl-1,3-butadiene

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 123299-03-6
2-[3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-4,7-diphenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
In 1,2-dichloro-ethane Heating;	73%
In 1,2-dichloro-ethane at 80℃; Rate constant; Thermodynamic data; Kinetics; other temp.; ΔH(excit.), ΔS(excit.);
In benzene at 60℃; Rate constant; var. reaction conditions: presence of gallium chloride;

: 6096-81-7
dimethyl iminodiacetate

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 5-[3-[1,3-dimethoxycarbonyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrol-5-yl]phenyl]-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With fullerene-C60; [5,6]fullerene-C70 In toluene at 60℃; for 12h; Irradiation;	67%

: 1468-95-7
9-hydroxymethylanthracene

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 1449506-15-3
C44H32N2O6

Conditions

Conditions	Yield
With Cu2(ADBTD)*(H2O)2 In ethanol at 50℃; for 24h; Catalytic behavior; Reagent/catalyst;	65%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 6-methyl-1-phenylhept-1-yn-3-one O-benzoyl oxime

: 2,2'-(1,3-phenylene)bis(7,7-dimethyl-8-phenyl-6,7-dihydrocyclopenta[e]pyrrolo[3,4-b]pyridine-1,3(2H,5H)-dione)

Conditions

Conditions	Yield
With sodium benzoate; iron(III)-acetylacetonate In 1,4-dioxane at 80℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere;	55%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 621-07-8
N,N-dibenzylhydroxylamine

A: 117022-12-5
1-{3-[3-(N,N-Dibenzyl-aminooxy)-2,5-dioxo-pyrrolidin-1-yl]-phenyl}-pyrrole-2,5-dione

B: 117022-11-4
C42H38N4O6

Conditions

Conditions	Yield
In tetrahydrofuran for 72h; Heating;	A 1.2 g B 46%

...Expand

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 5-chloro-N'-methyl-N'-(pyridin-2-yl)thiophene-2-carbohydrazide

: 7-chloro-2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)-4-(methyl(pyridin-2-yl)amino)-1H-pyrrolo[3,4-b]thieno[3,2-d]pyridine-1,3,5(2H,4H)-trione

Conditions

Conditions	Yield
With cobalt(II) diacetate tetrahydrate; sodium pivalate; silver carbonate In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube;	45%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 99-97-8
Dimethyl-p-toluidine

: 2,2'-(1,3-phenylene)bis(5,8-dimethyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione)

Conditions

Conditions	Yield
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In dimethyl sulfoxide at 50℃; for 24h;	34%

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 94-41-7
benzalacetophenone

: (E)-1-(3-(3-(2-cinnamoylphenyl)-2,5-dioxopyrrolidin-1-yl)phenyl)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In 1,2-dichloro-ethane at 100℃; for 6h; Inert atmosphere; Sealed tube;	33%

: 5471-63-6
1,3-diphenylisobenzofuran

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: C34H22N2O5

Conditions

Conditions	Yield
In 1,4-dioxane at 25℃; Rate constant; Thermodynamic data; Kinetics; other temp.; ΔH(excit.), ΔS(excit.);
In 1,4-dioxane at 25℃; Thermodynamic data; ΔH;
In 1,4-dioxane at 25℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), Ect, EA;

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 148058-43-9
1,7,11,17-Tetraaza-tricyclo[15.3.1.17,11]docosa-9,19-diene-8,18,21,22-tetraone

A: 9-{1-[3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-1,7,11,17-tetraaza-tricyclo[15.3.1.17,11]docosa-9,19-diene-8,18,21,22-tetraone

B: C50H52N10O12

Conditions

Conditions	Yield
With palladium diacetate In acetic acid at 80 - 90℃; for 6h;	A 0.177 g B 0.058 g

...Expand

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 148058-48-4
1,9,13,21-Tetraaza-tricyclo[19.3.1.19,13]hexacosa-11,23-diene-10,22,25,26-tetraone

A: 11-{1-[3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-1,9,13,21-tetraaza-tricyclo[19.3.1.19,13]hexacosa-11,23-diene-10,22,25,26-tetraone

B: 11,23-Bis-{1-[3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-1,9,13,21-tetraaza-tricyclo[19.3.1.19,13]hexacosa-11,23-diene-10,22,25,26-tetraone

Conditions

Conditions	Yield
With palladium diacetate In acetic acid at 80 - 90℃; for 6h;	A 0.190 g B 0.020 g

...Expand

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: C14H8N2O6

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; methyltrioxorhenium(VII) In toluene at 25℃; for 27h;

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 101-80-4
4,4'-oxydiphenylene diamine

: C38H32N6O6

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran at 50℃; for 18h; Solvent;

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 101-77-9
4,4'-diamino diphenyl methane

: C40H36N6O4

Conditions

Conditions	Yield
With acetic acid In acetone at 60℃; for 2h;

: 3006-93-7
N,N'-(1,3-phenylene)dimaleimide

: 101-77-9
4,4'-diamino diphenyl methane

: C54H56N6O10

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / acetone / 2 h / 60 °C 2: tetraethylammonium bromide; hydroquinone / 12 h / 60 °C View Scheme

N,N'-1,3-Phenylene bismaleimide Chemical Properties

IUPAC Name: 1-[3-(2,5-Dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione
Synonyms of 1,3-Bismaleimido benzene (CAS NO.3006-93-7): 1,3-Bismaleimidobenzene ;1,3-Dimaleimidobenzene ; 1,3-Phenylenebismaleimide ;1H-Pyrrole-2,5-dione, 1,1'-(phenylene)bis- ; N,N'-(m-Phenylene)bismaleimide ; N,N'-1,3-Phenylenedimaleimide ; N,N'-m-Phenylenemaleimide
CAS NO: 3006-93-7
Molecular Formula: C₁₄H₈N₂O₄
Molecular Weight: 268.23
Molecular Structure:
EINECS: 221-112-8
H bond acceptors: 6
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 74.76 Å²
Index of Refraction: 1.703
Molar Refractivity: 66.39 cm³
Molar Volume: 171 cm³
Surface Tension: 80.2 dyne/cm
Density: 1.567 g/cm³
Flash Point: 250.7 °C
Enthalpy of Vaporization: 76.77 kJ/mol
Boiling Point: 499.3 °C at 760 mmHg
Vapour Pressure: 4.2E-10 mmHg at 25°C
Melting point:198-201 °C(lit.)
Storage temp: Poison room
Water Solubility: negligible soluble
Appearance: yellow crystalline powder
Product Categories of 1,3-Bismaleimido benzene (CAS NO.3006-93-7): Curing Agent;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Acrylic Monomers;Maleimide;Monomers

N,N'-1,3-Phenylene bismaleimide Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	oral	250mg/kg (250mg/kg)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(11), Pg. 109, 1975.
rat	LC50	inhalation	55mg/m3/4H (55mg/m³)	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0790-1023S,
rat	LD50	oral	1370mg/kg (1370mg/kg)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(11), Pg. 109, 1975.
rat	LDLo	intraperitoneal	50mg/kg (50mg/kg)	National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 22, 1953.

N,N'-1,3-Phenylene bismaleimide Consensus Reports

Reported in EPA TSCA Inventory.

N,N'-1,3-Phenylene bismaleimide Safety Profile

Safety Information about 1,3-Bismaleimido benzene (CAS NO.3006-93-7):
Hazard Codes: Toxic T,T+. Irritant Xi
Risk Statements: 23/24/25-36/37/38-26-22
R22: Harmful if swallowed.
R26: Very toxic by inhalation.
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: 27-28-36/37/39-45-38
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S38: In case of insufficient ventilation, wear suitable respiratory equipment.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: ON6125000
Hazard Note: Irritant
Poison by ingestion, inhalation, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NO_x.

N,N'-1,3-Phenylene bismaleimide Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use foam, dry chemical, or carbon dioxide.
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container. Poison room locked.

Product Name

N,N'-1,3-Phenylene bismaleimide

Synthetic route

N,N'-1,3-Phenylene bismaleimide Chemical Properties

N,N'-1,3-Phenylene bismaleimide Toxicity Data With Reference

N,N'-1,3-Phenylene bismaleimide Consensus Reports

N,N'-1,3-Phenylene bismaleimide Safety Profile

N,N'-1,3-Phenylene bismaleimide Specification

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