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

N,N'-1,3-Phenylene bismaleimide

 EINECS 221-112-8
CAS No. 3006-93-7 Density 1.567 g/cm3
PSA 74.76000 LogP 0.67540
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 Molecular Structure of 3006-93-7 (N,N'-1,3-Phenylene bismaleimide) Hazard Symbols IrritantXi, ToxicT, VeryT+
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;

Article Data 14

N,N'-1,3-Phenylene bismaleimide Synthetic route

108-31-6

maleic anhydride

16674-78-5

magnesium(II) acetate tetrahydrate

3006-93-7

N,N'-(1,3-phenylene)dimaleimide

Conditions
ConditionsYield
With acetic anhydride In water; acetone84%
N,N'-m-phenylene-bis-malamic acid

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

3006-93-7

N,N'-(1,3-phenylene)dimaleimide

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

S01819

3006-93-7

N,N'-(1,3-phenylene)dimaleimide

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

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) Effect 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: ToxicT,T+.IrritantXi
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 NOx.

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.

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