3006-93-7

Basic information

• Product Name: N,N'-1,3-Phenylene bismaleimide
• Synonyms: 1,1’-(1,3-phenylene)bis-1h-pyrrole-5-dione;1,1’-(m-phenylene)bis-1h-pyrrole-2,5-dione;1,1’-(phenylene)bis-1h-pyrrole-5-dione;1,3-bismaleimidobenzene;1,3-dimaleimidobenzene;5-dione,1,1’-(1,3-phenylene)bis-1H-Pyrrole-2;hva2;hva-2curingagent
• CAS NO: 3006-93-7
• Molecular Formula: C₁₄H₈N₂O₄
• Molecular Weight: 268.22
• EINECS: 221-112-8
• Product Categories: Curing Agent;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Acrylic Monomers;Maleimide;Monomers;rubber additive;rubber auxiliary;Homobifunctional Crosslinker
• Mol File: 3006-93-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 198-201 °C(lit.)
• Boiling Point: 411.39°C (rough estimate)
• Flash Point: 250.7 °C
• Appearance: yellow crystalline powder
• Density: 1.3140 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5910 (estimate)
• Storage Temp.: Poison room
• PKA: -1.67±0.20(Predicted)
• Water Solubility: negligible soluble
• CAS DataBase Reference: N,N'-1,3-Phenylene bismaleimide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-1,3-Phenylene bismaleimide(3006-93-7)
• EPA Substance Registry System: N,N'-1,3-Phenylene bismaleimide(3006-93-7)

Safety Data

• Hazard Codes: T,Xi,T+
• Statements: 23/24/25-36/37/38-26-22
• Safety Statements: 27-28-36/37/39-45-38-28A
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: ON6125000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 3006-93-7(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

Different sources of media describe the Uses of 3006-93-7 differently. You can refer to the following data:
1. rubber vulcanizing agent; rubber crosslinkimg agent
2. N,N'-1,3-Phenylene bismaleimide and sulfur coordination to prevent reversion to improve the heat resistance, reduce heat, anti-aging, improve adhesion of the rubber and tire cord and vulcanized rubber modulus.PDM is a non-sulfur vulcanizing agents solve copper wire and copper electrical contacts because of sulfur vulcanizing agent to generate black copper sulfide pollution problems.

Flammability and Explosibility

Notclassified

Synthetic route

maleic anhydride (108-31-6) + magnesium(II) acetate tetrahydrate (16674-78-5) → N,N'-(1,3-phenylene)dimaleimide (3006-93-7)

Conditions	Yield
With acetic anhydride In water; acetone	84%

N,N'-m-phenylene-bis-malamic acid → N,N'-(1,3-phenylene)dimaleimide (3006-93-7)

Conditions	Yield
With sodium acetate; acetic anhydride

maleic anhydride (108-31-6) + m-phenylenediamine (108-45-2) → N,N'-(1,3-phenylene)dimaleimide (3006-93-7)

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

S01819 → N,N'-(1,3-phenylene)dimaleimide (3006-93-7)

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

5-p-tolyloxy-furan-2-carboxylic acid (60698-27-3) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → C36H24N2O6 (113452-03-2)

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 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	Yield
With tetrahexylammonium bromide; sodium carbonate In dichloromethane at 20℃; for 0.133333h; diastereoselective reaction;	92%

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 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	Yield
With silver orthophosphate; cobalt(II) diacetate tetrahydrate; sodium pivalate In 1,2-dichloro-ethane at 140℃; for 24h; Inert atmosphere; Sealed tube;	84%

3,3-dimethyl acrylaldehyde (107-86-8) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → 2,2′-(1,3-phenylene)bis(5-methylisoindoline-1,3-dione)

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

2-vinyloxy-1,3-butadiene (57796-76-6) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → 1,3-bis-(4-vinyloxy-Δ4-tetrahydrophthalimido)benzene (88848-43-5)

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + phenylhydrazone of ethyl ester of glyoxalic acid (80447-71-8) → 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	Yield
With copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 2h;	76%

trans,trans-1,4-Diphenyl-1,3-butadiene (886-65-7, 538-81-8) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → 2-[3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-4,7-diphenyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione (123299-03-6)

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;

dimethyl iminodiacetate (6096-81-7) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → 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	Yield
With fullerene-C60; [5,6]fullerene-C70 In toluene at 60℃; for 12h; Irradiation;	67%

9-hydroxymethylanthracene (1468-95-7) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → C44H32N2O6 (1449506-15-3)

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 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	Yield
With sodium benzoate; iron(III)-acetylacetonate In 1,4-dioxane at 80℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere;	55%

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + N,N-dibenzylhydroxylamine (621-07-8) → 1-{3-[3-(N,N-Dibenzyl-aminooxy)-2,5-dioxo-pyrrolidin-1-yl]-phenyl}-pyrrole-2,5-dione (117022-12-5) + C42H38N4O6 (117022-11-4)

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 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	Yield
With cobalt(II) diacetate tetrahydrate; sodium pivalate; silver carbonate In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube;	45%

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + Dimethyl-p-toluidine (99-97-8) → 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	Yield
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In dimethyl sulfoxide at 50℃; for 24h;	34%

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + benzalacetophenone (94-41-7) → (E)-1-(3-(3-(2-cinnamoylphenyl)-2,5-dioxopyrrolidin-1-yl)phenyl)-1H-pyrrole-2,5-dione

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%

1,3-diphenylisobenzofuran (5471-63-6) + N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → C34H22N2O5

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;

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 1,7,11,17-Tetraaza-tricyclo[15.3.1.17,11]docosa-9,19-diene-8,18,21,22-tetraone (148058-43-9) → 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 + C50H52N10O12

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 1,9,13,21-Tetraaza-tricyclo[19.3.1.19,13]hexacosa-11,23-diene-10,22,25,26-tetraone (148058-48-4) → 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 + 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	Yield
With palladium diacetate In acetic acid at 80 - 90℃; for 6h;	A 0.190 g B 0.020 g

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) → C14H8N2O6

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 4,4'-oxydiphenylene diamine (101-80-4) → C38H32N6O6

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 4,4'-diamino diphenyl methane (101-77-9) → C40H36N6O4

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

N,N'-(1,3-phenylene)dimaleimide (3006-93-7) + 4,4'-diamino diphenyl methane (101-77-9) → C54H56N6O10

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

Upstream product

• 13161-99-4 S₀₁₈₁₉ 
• 108-31-6 maleic anhydride 
• 108-45-2 m-phenylenediamine 
• 16674-78-5 magnesium(II) acetate tetrahydrate 

Downstream Products

• 113452-03-2 C₃₆H₂₄N₂O₆ 

Relevant articles and documents

A N, inter-N' - phenylene bismaleimide preparation method

The invention discloses a N, inter-N' - phenylene bismaleimide preparation method, which belongs to the technical field of fine chemicals. The raw material is toluene, maleic anhydride and the polymerization inhibitor, heated to 40 - 60 °C dissolve; the metaphenylene diamine dissolved in strong polar solvent then drop added in a reaction vessel, and milling after thermal insulation, adding catalyst heating temperature to reflux, until no more water is stopped when the reaction is separated out; the reaction cooling after crystallization, filtered, washed with water, to obtain pale yellow solid N, between the N' - phenylene bismaleimide. The invention two-step reaction in the same reaction in the container, does not need to separation and purification of the intermediate product, its synthesis process is simple in operation, the working environment is obviously improved. The sold product liquid chromatography the content of 75% -80%, for the production of this invention liquid chromatography content can be up to 90% or more, the purity is higher than current commercial products.

Process for the preparation of aromatic maleimides

Aromatic maleimides can be prepared by reacting corresponding aromatic amines with maleic anhydride in the presence of a solvent mixture of halogenated hydrocarbon and a dipolar aprotic solvent, with the addition of acid and a polymerization inhibitor.

Curable mixtures based on maleimides and propenyl-substituted phenols, and the use thereof

Curable mixtures of (a) maleimides of the general formula I STR1 wherein R is an n-valent aliphatic or aromatic radical, and n is the number 1, 2 or 3; and (b) mono- or polyvalent phenols which contain in the molecule at least one 1-propenyl group in the ortho- or para-position with respect to the hydroxyl group, or isomeric mixtures of mono- or polyvalent phenols which are propenyl-substituted in the ortho- or para-position and mono- or polyvalent phenols which are allyl-substituted in the ortho- or para-position, the proportion of propenyl groups in the isomeric mixture having to be at least 5 equivalent-%, relative to the sum of the equivalents of propenyl and allyl groups. The novel mixtures cure at elevated temperatures relatively rapidly, and produce molded materials having valuable mechanical properties.