1-[4-(1H-1,3-benzodiazol-2-yl)phenyl]-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 156077
• Molecular Formular: C17H11N3O2
• Molecular Mass: 289.28814
• Monoisotopic Mass: 289.08512661
• SMILES: c1ccc2c(c1)[nH]c(n2)c1ccc(cc1)N1C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1c1ccc(cc1)c1nc2c([nH]1)cccc2
• InChI: InChI=1S/C17H11N3O2/c21-15-9-10-16(22)20(15)12-7-5-11(6-8-12)17-18-13-3-1-2-4-14(13)19-17/h1-10H,(H,18,19)
• InChIKey: NZDOXVCRXDAVII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(1H-1,3-benzodiazol-2-yl)phenyl]-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-[4-(1H-1,3-benzodiazol-2-yl)phenyl]pyrrole-2,5-dione
• Synonyms: BIPM; N-[4-(2-Benzimidazolyl)phenyl]maleimide

Database IDs

• CAS Number: 27030-97-3
• EC Number: 248-173-3
• MDL Number: MFCD00042767
• Beilstein Number: 755407
• PubChem SID: 162250215; 24847500
• PubChem CID: 117909

CALCULATED PROPERTIES

• Acid pKa: 11.490391
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.406802
• LogD (pH = 7.4): 2.5544443
• Log P: 2.55676
• Molar Refractivity: 92.0378 cm^3
• Polarizability: 32.58289 Å^3
• Polar Surface Area: 66.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 315 nm; λem 365 nm (after derivatization with 2-mercaptoethanol)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C17H11N3O2

DETAILS

Sigma Aldrich - 12266

Other Notes
Fluorescent probe in proteins, used for microfluorometry of thiol compounds (detection limit: 10-6 m thiol conc.)1; Review2,3
Packaging
1 mg in poly bottle