1-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 91537
• Molecular Formular: C14H8N2O4
• Molecular Mass: 268.22432
• Monoisotopic Mass: 268.04840675
• SMILES: N1(c2ccc(cc2)N2C(=O)C=CC2=O)C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1c1ccc(cc1)N1C(=O)C=CC1=O
• InChI: InChI=1S/C14H8N2O4/c17-11-5-6-12(18)15(11)9-1-2-10(4-3-9)16-13(19)7-8-14(16)20/h1-8H
• InChIKey: AQGZJQNZNONGKY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione
• Synonyms: 1,4-Dimaleimidobenzene; N,N′-(p-Phenylene)dimaleimide; N,N′-(1,4-Phenylene)dimaleimide; 1,1'-Benzene-1,4-diylbis(1H-pyrrole-2,5-dione); N,N'-Benzene-1,4-dimaleimide; 1,4-PDM; p-N,N'-Phenylenebismaleimide; p-Phenylene Dimaleimide; 1,4-Bismaleimidobenzene; 1,4-Phenylenebismaleimide; 4,4'-Phenylenedimaleimide; N,N'-1,4-Phenylenebismaleimide; 1,4-Phenylene-bis-maleimide; N,N'-p-PHENYLENE-DIMALEIMIDE; N,N′-(对亚苯基)二马来酰亚胺; N,N′-(1,4-亚苯基)二马来酰亚胺

Database IDs

• CAS Number: 3278-31-7
• EC Number: 221-910-6
• MDL Number: MFCD00005505
• Beilstein Number: 249631
• PubChem SID: 24887314; 24898322; 162078236
• PubChem CID: 76765

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.51821566
• LogD (pH = 7.4): 0.5182173
• Log P: 0.5182174
• Molar Refractivity: 69.9934 cm^3
• Polarizability: 25.71558 Å^3
• Polar Surface Area: 74.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: >300 °C(lit.); >300°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC); 97%
• Empirical Formula (Hill Notation): C14H8N2O4

DETAILS

MP Biomedicals - 02156171

Light yellow crystals.

Sigma Aldrich - P23989

Packaging
10 g in glass bottle

Sigma Aldrich - 78485

Other Notes
Bifunctional thiol reagent for the cross-linking of proteins1; Efficient procedure for the conjugation of an antibody with an enzyme2,3,4

Toronto Research Chemicals - P319810

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

REFERENCES

• Knight, P., et al.: Biochem. J., 179, 191 (1979)
• Yoshitake, S., et al.: Scand. J. Immun., 10, 81 (1979)