5-(bromomethyl)-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase ID: 155940
• Molecular Formular: C21H13BrO5
• Molecular Mass: 425.22892
• Monoisotopic Mass: 423.99463552
• SMILES: c1cc2c(cc1CBr)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• Canonical SMILES: BrCc1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• InChI: InChI=1S/C21H13BrO5/c22-10-11-1-4-15-14(7-11)20(25)27-21(15)16-5-2-12(23)8-18(16)26-19-9-13(24)3-6-17(19)21/h1-9,23-24H,10H2
• InChIKey: OQHKPJAZGYJYTB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(bromomethyl)-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 5-(bromomethyl)-3',6'-dihydroxyspiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: 5-BMF; 5-(Bromomethyl)fluorescein

Database IDs

• CAS Number: 148942-72-7
• PubChem SID: 162250078
• PubChem CID: 132858

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.6528196
• LogD (pH = 7.4): 4.632623
• Log P: 4.65308
• Molar Refractivity: 104.0705 cm^3
• Polarizability: 38.946396 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 492 nm; λem 515 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% (sum of tautomers, GC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C21H13BrO5

DETAILS

Sigma Aldrich - 72755

Other Notes
Labeling of nucleosides and nucleotides at the N-atom1; labeling of carboxylic acids: shows very strong absorption and fluorescence2,3.