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

• ChemBase ID: 154998
• Molecular Formular: C22H18F3N3O7S
• Molecular Mass: 525.4544296
• Monoisotopic Mass: 525.08175559
• SMILES: COc1ccc(cc1)c1cnc(o1)c1cc[n+](cc1)CCN1C(=O)C=CC1=O.C(F)(F)(F)S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)C(F)(F)F.COc1ccc(cc1)c1cnc(o1)c1cc[n+](cc1)CCN1C(=O)C=CC1=O
• InChI: InChI=1S/C21H18N3O4.CHF3O3S/c1-27-17-4-2-15(3-5-17)18-14-22-21(28-18)16-8-10-23(11-9-16)12-13-24-19(25)6-7-20(24)26;2-1(3,4)8(5,6)7/h2-11,14H,12-13H2,1H3;(H,5,6,7)/q+1;/p-1
• InChIKey: LVIALPCMAFGHPU-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 155862-98-9
• MDL Number: MFCD08276998
• PubChem SID: 24864002; 162249136
• PubChem CID: 10256297

CALCULATED PROPERTIES

• Acid pKa: 17.43063
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -2.395334
• LogD (pH = 7.4): -2.39533
• Log P: -2.39533
• Molar Refractivity: 113.6235 cm^3
• Polarizability: 40.752876 Å^3
• Polar Surface Area: 76.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 397 nm; λem 569 nm in 0.1 M phosphate pH 7.0

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-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): C22H18F3N3O7S

DETAILS

Sigma Aldrich - 38463

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