4-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-oxazol-5-yl]-1-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]pyridin-1-ium trifluoromethanesulfonate

• ChemBase ID: 155008
• Molecular Formular: C24H20F3N3O7S
• Molecular Mass: 551.4917096
• Monoisotopic Mass: 551.09740566
• SMILES: c1cc2c(cc1c1ncc(o1)c1cc[n+](cc1)CCN1C(=O)C=CC1=O)CCCO2.C(F)(F)(F)S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)C(F)(F)F.O=C1C=CC(=O)N1CC[n+]1ccc(cc1)c1cnc(o1)c1ccc2c(c1)CCCO2
• InChI: InChI=1S/C23H20N3O4.CHF3O3S/c27-21-5-6-22(28)26(21)12-11-25-9-7-16(8-10-25)20-15-24-23(30-20)18-3-4-19-17(14-18)2-1-13-29-19;2-1(3,4)8(5,6)7/h3-10,14-15H,1-2,11-13H2;(H,5,6,7)/q+1;/p-1
• InChIKey: FGUKXLKALCIXHR-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-oxazol-5-yl]-1-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]pyridin-1-ium trifluoromethanesulfonate
• IUPAC Traditional name: 4-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-oxazol-5-yl]-1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyridin-1-ium triflate
• Synonyms: 1-[2-(Maleimido)ethyl]-4-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-oxazolyl]pyridinium triflate

Database IDs

• CAS Number: 155863-05-1
• MDL Number: MFCD08276999
• PubChem SID: 162249146; 24864029
• PubChem CID: 10076268

CALCULATED PROPERTIES

• Acid pKa: 17.952803
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.9108772
• LogD (pH = 7.4): -1.9108728
• Log P: -1.9108727
• Molar Refractivity: 121.5341 cm^3
• Polarizability: 43.628994 Å^3
• Polar Surface Area: 76.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 389 nm; λem 528 nm in 0.1 M phosphate pH 7.0

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPCE)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C24H20F3N3O7S

DETAILS

Sigma Aldrich - 38548

General description
New class of highly photostable, water soluble fluorescent labels with large Stoke′s shift, high QY in aqueous media and pH tolerance. Major disadvantage: rel. low extinction coefficient (Ε slightly >20′000 in EtOH)1.