4-carboxy-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2,2,6,6-tetramethylpiperidin-1-ium-1-olate

• ChemBase ID: 169339
• Molecular Formular: C25H29N2O5
• Molecular Mass: 437.50816
• Monoisotopic Mass: 437.20764704
• SMILES: C1C([N+](C(CC1(NC(=O)OCC1c2c(c3c1cccc3)cccc2)C(=O)O)(C)C)[O-])(C)C
• Canonical SMILES: O=C(NC1(CC(C)(C)[N+](C(C1)(C)C)[O-])C(=O)O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C25H30N2O5/c1-23(2)14-25(21(28)29,15-24(3,4)27(23)31)26-22(30)32-13-20-18-11-7-5-9-16(18)17-10-6-8-12-19(17)20/h5-12,20,27H,13-15H2,1-4H3,(H,26,30)(H,28,29)
• InChIKey: KSZSHFKNYIGTIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-carboxy-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2,2,6,6-tetramethylpiperidin-1-ium-1-olate
• IUPAC Traditional name: 4-carboxy-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2,2,6,6-tetramethylpiperidin-1-ium-1-olate
• Synonyms: Fmoc-TOAC; Fmoc-2,2,6,6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic Acid

Database IDs

• CAS Number: 93372-25-9
• PubChem SID: 162263471
• PubChem CID: 71316915

CALCULATED PROPERTIES

• Acid pKa: 3.7595367
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.7614455
• LogD (pH = 7.4): -4.3093305
• Log P: -1.0788572
• Molar Refractivity: 130.4512 cm^3
• Polarizability: 47.81578 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow Solid
• Melting Point: 162-164°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F675000

A stable free radical spin label.

REFERENCES

• Marchetto, R. et al.: J.A.C.S., 115, 11042 (1993)
• J. Org. Chem., 64, 9118 (1993)
• Millhauser, et al.: J. Am. Chem. Soc., 121, 11071 (1999)