1-[(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)methyl]-4-[5-(4-methoxyphenyl)-1,3-oxazol-2-yl]pyridin-1-ium bromide

• ChemBase ID: 154996
• Molecular Formular: C27H22BrN3O6
• Molecular Mass: 564.38408
• Monoisotopic Mass: 563.06919744
• SMILES: COc1ccc(cc1)c1cnc(o1)c1cc[n+](cc1)Cc1cccc(c1)C(=O)ON1C(=O)CCC1=O.[Br-]
• Canonical SMILES: COc1ccc(cc1)c1cnc(o1)c1cc[n+](cc1)Cc1cccc(c1)C(=O)ON1C(=O)CCC1=O.[Br-]
• InChI: InChI=1S/C27H22N3O6.BrH/c1-34-22-7-5-19(6-8-22)23-16-28-26(35-23)20-11-13-29(14-12-20)17-18-3-2-4-21(15-18)27(33)36-30-24(31)9-10-25(30)32;/h2-8,11-16H,9-10,17H2,1H3;1H/q+1;/p-1
• InChIKey: DENNAQTZCPWYSQ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)methyl]-4-[5-(4-methoxyphenyl)-1,3-oxazol-2-yl]pyridin-1-ium bromide
• IUPAC Traditional name: 1-[(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)methyl]-4-[5-(4-methoxyphenyl)-1,3-oxazol-2-yl]pyridin-1-ium bromide
• Synonyms: 1-[3-(Succinimidyloxycarbonyl)benzyl]-4-[5-(4-methoxyphenyl)-2-oxazolyl]pyridinium bromide

Database IDs

• CAS Number: 155862-95-6
• MDL Number: MFCD00467811
• PubChem SID: 24867535; 162249134
• PubChem CID: 10209875

CALCULATED PROPERTIES

• Acid pKa: 17.697292
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.85994214
• LogD (pH = 7.4): -0.8599368
• Log P: -0.8599367
• Molar Refractivity: 139.767 cm^3
• Polarizability: 51.245625 Å^3
• Polar Surface Area: 102.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 399 nm; λem 575 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: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C27H22BrN3O6

DETAILS

Sigma Aldrich - 43973

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.