3-(1,3-benzothiazol-2-yl)-7-hydroxy-2H-chromen-2-one

• ChemBase ID: 156193
• Molecular Formular: C16H9NO3S
• Molecular Mass: 295.31256
• Monoisotopic Mass: 295.03031415
• SMILES: c1ccc2c(c1)nc(s2)c1cc2ccc(cc2oc1=O)O
• Canonical SMILES: Oc1ccc2c(c1)oc(=O)c(c2)c1nc2c(s1)cccc2
• InChI: InChI=1S/C16H9NO3S/c18-10-6-5-9-7-11(16(19)20-13(9)8-10)15-17-12-3-1-2-4-14(12)21-15/h1-8,18H
• InChIKey: CYONGLVNBSZCQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1,3-benzothiazol-2-yl)-7-hydroxy-2H-chromen-2-one
• IUPAC Traditional name: 3-(1,3-benzothiazol-2-yl)-7-hydroxychromen-2-one
• Synonyms: 3-(2-Benzothiazolyl)-7-hydroxycoumarin; 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one; Coumarin 16; 3-(2-Benzothiazolyl)umbelliferone

Database IDs

• CAS Number: 58851-99-3
• MDL Number: MFCD00037411
• Beilstein Number: 545429
• PubChem SID: 24847801; 162250331
• PubChem CID: 5398639

CALCULATED PROPERTIES

• Acid pKa: 7.730084
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6631198
• LogD (pH = 7.4): 3.5003214
• Log P: 3.665653
• Molar Refractivity: 78.5295 cm^3
• Polarizability: 31.263433 Å^3
• Polar Surface Area: 59.42 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; DMF: soluble; DMSO: soluble
• Melting Point: 290-292 °C(lit.)
• pKa: 7.0
• Fluorescence: λex 385 nm; λem 490 nm in 0.1 M Tris pH 10.0

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): C16H9NO3S

DETAILS

Sigma Aldrich - 12787

Application
suitable as pH-indicator