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
• Article Data: 3

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

• 1567324-59-7 (3aR,6aS)(Z/E)-5-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-phenyl)-2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]dithiolo[3,4-b]-[1,4]thiazin-5(6H)-ylidene)dihydro-4H-[1,3]dithiolo[4,5-c]-pyrrole-4,6(5H)-dione 
• 1567324-61-1 (3aR,6aS)(Z/E)-2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]-dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-5-(4-((3aR,6aS)(E/Z)-2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]dithiolo[3,4-b][1,4]-thiazin-5(6H)-ylidene)-4,6-dioxotetrahydro-5H-[1,3]dithiolo-[4,5-c]pyrrol-5-yl)phenyl)dihydro-4H-[1,3]dithiolo[4,5-c]-pyrrole-4,6(5H)-dione 
• 1251005-20-5 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3a,6a-dihydro-3-(4-nitrophenyl)-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1251005-13-6 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3-(4-bromophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1251005-12-5 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3-(4-chlorophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1251005-16-9 (3aR,6aR,3a'S,6a'S)-5,5'-(1,4-phenylene)bis[3a,6a-dihydro-3-(4-methylphenyl)-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] 
• 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] 
• 1251005-11-4 (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) 
• 1251005-22-7 (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] 

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.

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.