2,5-dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate

• ChemBase ID: 155888
• Molecular Formular: C18H18N2O6
• Molecular Mass: 358.34532
• Monoisotopic Mass: 358.11648631
• SMILES: CCN(CC)c1ccc2cc(c(=O)oc2c1)C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: CCN(c1ccc2c(c1)oc(=O)c(c2)C(=O)ON1C(=O)CCC1=O)CC
• InChI: InChI=1S/C18H18N2O6/c1-3-19(4-2)12-6-5-11-9-13(17(23)25-14(11)10-12)18(24)26-20-15(21)7-8-16(20)22/h5-6,9-10H,3-4,7-8H2,1-2H3
• InChIKey: NUNPVRICKDZFLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxochromene-3-carboxylate
• Synonyms: N-Succinimidyl 7-(diethylamino)coumarin-3-carboxylate; 7-(Diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester

Database IDs

• CAS Number: 139346-57-9
• MDL Number: MFCD00467585
• Beilstein Number: 5359433
• PubChem SID: 24862878; 162250026
• PubChem CID: 2760552

CALCULATED PROPERTIES

• Acid pKa: 17.696003
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.7772769
• LogD (pH = 7.4): 1.7949511
• Log P: 1.7951812
• Molar Refractivity: 92.1025 cm^3
• Polarizability: 34.834736 Å^3
• Polar Surface Area: 93.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; DMF: soluble; DMSO: soluble
• Fluorescence: λex 445 nm; λem 482 nm in 0.1 M phosphate pH 7.0

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC)
• Suitability: corresponds for coupling to amines; suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C18H18N2O6

DETAILS

Sigma Aldrich - 36801

Other Notes
Labeling of amino acids prior to resolution by capillary zone electrophoresis1