5-isothiocyanato-2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 155846
• Molecular Formular: C21H7Br4NO5S
• Molecular Mass: 704.96498
• Monoisotopic Mass: 700.67784133
• SMILES: c1cc(c(cc1N=C=S)C(=O)O)c1c2cc(c(c(c2oc2c(c(=O)c(cc12)Br)Br)Br)O)Br
• Canonical SMILES: S=C=Nc1ccc(c(c1)C(=O)O)c1c2cc(Br)c(c(c2oc2c1cc(Br)c(=O)c2Br)Br)O
• InChI: InChI=1S/C21H7Br4NO5S/c22-12-4-10-14(8-2-1-7(26-6-32)3-9(8)21(29)30)11-5-13(23)18(28)16(25)20(11)31-19(10)15(24)17(12)27/h1-5,27H,(H,29,30)
• InChIKey: MCXYFYWNOWPDMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-isothiocyanato-2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 5-isothiocyanato-2-(2,4,5,7-tetrabromo-3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• Synonyms: EITC; Eosin 5-isothiocyanate

Database IDs

• CAS Number: 60520-47-0
• MDL Number: MFCD00082502
• PubChem SID: 162249984; 24868702
• PubChem CID: 5218603

CALCULATED PROPERTIES

• Acid pKa: 3.0756483
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.293053
• LogD (pH = 7.4): 1.7380224
• Log P: 6.8807483
• Molar Refractivity: 150.9397 cm^3
• Polarizability: 51.80441 Å^3
• Polar Surface Area: 96.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 521; λem 544 (pH 9.0)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42
• Safety Statements: 22-24/25
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (UV)
• Empirical Formula (Hill Notation): C21H7Br4NO5S

DETAILS

Sigma Aldrich - 45245

Other Notes
Acceptor fluorophore. Measurement of rotational diffusion of proteins1; In fluorescence energy transfer studies2,3