3-(1,3-benzoxazol-2-yl)-7-hydroxy-2-oxo-2H-chromene-4-carbonitrile

• ChemBase ID: 155938
• Molecular Formular: C17H8N2O4
• Molecular Mass: 304.25642
• Monoisotopic Mass: 304.04840675
• SMILES: c1ccc2c(c1)nc(o2)c1c(c2ccc(cc2oc1=O)O)C#N
• Canonical SMILES: N#Cc1c(c(=O)oc2c1ccc(c2)O)c1nc2c(o1)cccc2
• InChI: InChI=1S/C17H8N2O4/c18-8-11-10-6-5-9(20)7-14(10)23-17(21)15(11)16-19-12-3-1-2-4-13(12)22-16/h1-7,20H
• InChIKey: FJBJRHZSCDFLBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1,3-benzoxazol-2-yl)-7-hydroxy-2-oxo-2H-chromene-4-carbonitrile
• IUPAC Traditional name: 3-(1,3-benzoxazol-2-yl)-7-hydroxy-2-oxochromene-4-carbonitrile
• Synonyms: 3-(2-Benzoxazolyl)-4-cyano-7-hydroxycoumarin; 3-(2-Benzoxazolyl)-4-cyanoumbelliferone

Database IDs

• CAS Number: 90146-01-3
• MDL Number: MFCD01862928
• Beilstein Number: 6431927
• PubChem SID: 162250076; 24847838
• PubChem CID: 6116680

CALCULATED PROPERTIES

• Acid pKa: 6.9356093
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5722141
• LogD (pH = 7.4): 2.0037072
• Log P: 2.5877492
• Molar Refractivity: 79.1024 cm^3
• Polarizability: 31.149021 Å^3
• Polar Surface Area: 96.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; methanol: soluble
• Melting Point: 282-285 °C(lit.)
• Fluorescence: λex 505 nm; λem 577 nm in 0.1 M Tris pH 9.0

Safety Information

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

Product Information

• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C17H8N2O4

DETAILS

Sigma Aldrich - 12826

Other Notes
Long wave absorbing and fluorescing pH indicator for the weakly acidic pH range, and enzyme substrate ref. standard1