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

• ChemBase ID: 157842
• Molecular Formular: C12H12N2O4
• Molecular Mass: 248.23468
• Monoisotopic Mass: 248.07970687
• SMILES: C1=CC(=O)N(C1=O)CCCCN1C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1CCCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C12H12N2O4/c15-9-3-4-10(16)13(9)7-1-2-8-14-11(17)5-6-12(14)18/h3-6H,1-2,7-8H2
• InChIKey: WXXSHAKLDCERGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl]-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-[4-(2,5-dioxopyrrol-1-yl)butyl]pyrrole-2,5-dione
• Synonyms: 1,1'-(1,4-Butanediyl)bis-1H-pyrrole-2,5-dione; Tetramethylenedimaleimide; Tetramethylenebismaleimide; N,N'-Tetramethylenedi-maleimide; NSC 44747; 1,4-Bis(maleimido)butane; 1,4-Bis(maleimido)butane; BMB; N,N′-(Tetramethylene)dimaleimide; 1,4-Di(maleimido)butane

Database IDs

• CAS Number: 28537-70-4
• MDL Number: MFCD01318342
• Beilstein Number: 1538100
• PubChem SID: 162251978; 24887583
• PubChem CID: 239576

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.41865626
• LogD (pH = 7.4): -0.41865626
• Log P: -0.41865626
• Molar Refractivity: 64.0372 cm^3
• Polarizability: 23.561218 Å^3
• Polar Surface Area: 74.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Powder
• Melting Point: 196-197°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C12H12N2O4

DETAILS

Sigma Aldrich - 80805

Application
Linker for preparing biomimetics: J. Med. Chem. 35, 1563 (1992)

Toronto Research Chemicals - B475000

A short, sulfhydryl reactive homobifunctional crosslinking reagent.

REFERENCES

• Jahng, W., et al.: Biochem., 41, 7528 (2002)