3-(5-chloro-1,3-benzoxazol-2-yl)-7-hydroxy-2-oxo-2H-chromene-4-carbonitrile

• ChemBase ID: 156307
• Molecular Formular: C17H7ClN2O4
• Molecular Mass: 338.70148
• Monoisotopic Mass: 338.00943439
• SMILES: c1cc2c(cc1O)oc(=O)c(c2C#N)c1nc2cc(ccc2o1)Cl
• Canonical SMILES: N#Cc1c(c(=O)oc2c1ccc(c2)O)c1oc2c(n1)cc(cc2)Cl
• InChI: InChI=1S/C17H7ClN2O4/c18-8-1-4-13-12(5-8)20-16(23-13)15-11(7-19)10-3-2-9(21)6-14(10)24-17(15)22/h1-6,21H
• InChIKey: MEQPFAHGQRHYMD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(5-chloro-1,3-benzoxazol-2-yl)-7-hydroxy-2-oxo-2H-chromene-4-carbonitrile
• IUPAC Traditional name: 3-(5-chloro-1,3-benzoxazol-2-yl)-7-hydroxy-2-oxochromene-4-carbonitrile
• Synonyms: 3-(5-Chloro-2-benzoxazolyl)-4-cyano-7-hydroxycoumarin; 3-(5-Chloro-2-benzoxazolyl)-4-cyanoumbelliferone

Database IDs

• CAS Number: 97477-81-1
• MDL Number: MFCD00674504
• Beilstein Number: 5992861
• PubChem SID: 162250445; 24854229
• PubChem CID: 5998498

CALCULATED PROPERTIES

• Acid pKa: 6.9356093
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1762588
• LogD (pH = 7.4): 2.6077518
• Log P: 3.191794
• Molar Refractivity: 83.9072 cm^3
• Polarizability: 33.05247 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: 291-294 °C(lit.)
• pKa: 6.0
• Fluorescence: λex 497 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

• Purity: ≥95% (TLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C17H7ClN2O4

DETAILS

Sigma Aldrich - 23724

Application
suitable as pH-indicator
Other Notes
Longwave absorbing and fluorescing pH indicator, and enzyme substrate ref. standard1