3278-31-7

Basic information

• Product Name: N,N'-1,4-PHENYLENEDIMALEIMIDE
• Synonyms: N,N'-P-PHENYLENEDIMALEIMIDE;N,N'-1,4-PHENYLENEBISMALEIMIDE;N,N'-1,4-PHENYLENEDIMALEIMIDE;N,N'-1,4-BISMALEIMIDOBENZENE;n,n’-4-phenylenedimaleimide;1,4-DIMALEIMIDOBENZENE;1,4-PHENYLENE-BIS-MALEIMIDE;1,4-PDM
• CAS NO: 3278-31-7
• Molecular Formula: C₁₄H₈N₂O₄
• Molecular Weight: 268.22
• EINECS: 221-910-6
• Product Categories: Maleimide Derivatives;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Cross Linking Reagents;MTS & Sulfhydryl Active Reagents;Homobifunctional Crosslinker
• Mol File: 3278-31-7.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 411.39°C (rough estimate)
• Flash Point: 250.7 °C
• Appearance: Off-White Solid
• Density: 1.3140 (rough estimate)
• Refractive Index: 1.5910 (estimate)
• Storage Temp.: Poison room
• Solubility: DMSO, Methanol (Very Slightly)
• PKA: -1.81±0.20(Predicted)
• BRN: 249631
• CAS DataBase Reference: N,N'-1,4-PHENYLENEDIMALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-1,4-PHENYLENEDIMALEIMIDE(3278-31-7)
• EPA Substance Registry System: N,N'-1,4-PHENYLENEDIMALEIMIDE(3278-31-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 45-38-36/37/39-28A
• WGK Germany: 3
• Hazardous Substances Data: 3278-31-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A short, sulfhydryl reactive hmombifunctional crosslinking reagent for protein crosslinking.

Upstream product

• 108-31-6 maleic anhydride 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 92176-74-4 1,4-bis<3-(3,5-di-t-butyl-4-hydroxyphenylthio)-2,5-dioxopyrrolidin-1-yl>benzene 
• 112275-45-3 (1R,2S,6R,7S)-1,7,8,9,10,10-Hexabromo-4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 112252-86-5 (1S,2S,6R,7R)-1,7,8,9-Tetrabromo-4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-10,10-dimethoxy-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 109839-45-4 C₇₂H₆₄N₂O₈ 
• 1251005-22-7 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3a,6a-dihydro-1-phenyl-3-[4-(trifluoromethyl)phenyl]pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1251005-11-4 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis(3a,6a-dihydro-1,3-diphenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione) 
• 1251005-21-6 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3a,6a-dihydro-3-(4-methoxyphenyl)-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1251005-19-2 (3aR,6aR,3a'S,6a'S)-4,4'-[(4,1-phenylene)bis(3a,4,6,6a-tetrahydro-4,6-dioxo-1-phenylpyrrolo[3,4-c]pyrazole-5,3(1H)-diyl)]bis[benzonitrile] 

Relevant articles and documents

Synthesis, UV-Vis spectra, and Hammett correlation of some novel bis(dihydropyrrolo[3,4-c]pyrazoles)

Twenty-nine novel bis(dihydropyrrolo[3,4-c]pyrazole) derivatives were obtained by reacting C, N-phenyl-substituted nitrilimines generated in situ from corresponding hydrazonyl chlorides with bismaleimides. The structures were elucidated by physical and spectroscopic methods [m.p., Rf, infrared (IR),1H nuclear magnetic resonance (NMR), 13C NMR, correlation spectroscopy (COSY), heteronuclear correlation (HETCOR), nuclear Overhauser effect (NOE), and high-resolution mass spectrometry (HRMS)]. Also, Hammett correlation graphs were obtained between Hammett constants σp and λmax values of bis(pyrrolopyrazoles) carrying p-substituted phenyl-ring-bearing electron-withdrawing and electrondonating groups and discussed in terms of substituent effects. Springer-Verlag 2010.

Functional monomaleimide and thermosetting composition therefrom

Novel N-(meth)allyloxyphenylmaleimides are prepolymerized with at least one bis-imide and formulated, together with at least one imidazole compound, into thermosetting compositions useful for the production of a wide variety of shaped articles having improved mechanical properties.

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.