bis(pyridin-1-ium-1-yl)iodanium; tetrafluoroboranuide

• ChemBase ID: 302584
• Molecular Formular: C10H10BF4IN2++
• Molecular Mass: 371.9088828
• Monoisotopic Mass: 371.99178961
• SMILES: [B-](F)(F)(F)F.c1cc[n+](cc1)[I+][n+]1ccccc1
• Canonical SMILES: c1cc[n+](cc1)[I+][n+]1ccccc1.F[B-](F)(F)F
• InChI: InChI=1S/C10H10IN2.BF4/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13;2-1(3,4)5/h1-10H;/q+3;-1
• InChIKey: MYBIVUDNVYMZMI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(pyridin-1-ium-1-yl)iodanium; tetrafluoroboranuide
• IUPAC Traditional name: bis(pyridin-1-ium-1-yl)iodanium tetrafluoroborate
• Synonyms: Barluenga's Reagent; Bis(pyridine)iodonium tetrafluoroborate; 双(吡啶)四氟硼化碘

Database IDs

• CAS Number: 15656-28-7
• MDL Number: MFCD03703393
• Beilstein Number: 4284739

CALCULATED PROPERTIES

• Acid pKa: 14.295667
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -2.9395175
• LogD (pH = 7.4): -2.9395175
• Log P: -2.9395175
• Molar Refractivity: 64.8818 cm^3
• Polarizability: 28.133 Å^3
• Polar Surface Area: 7.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ca 160°C dec.

Safety Information

• Storage Warning: Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P280G-P305+P351+P338

Product Information

• Purity: 97%

REFERENCES

• Powerful electrophilic iodinating agent; reagent of choice for selective iodinations, under mild conditions, of alkenes: Angew. Chem. Int. Ed., 27, 1715 (1985), acetylenes: J. Org. Chem., 55, 3104 (1990), and aromatic compounds: J. Org. Chem., 58, 2058 (1993); Tetrahedron Lett., 34, 3893 (1993).
• Useful for selective iodination of free phenolic groups in tyrosine residues during solid-phase synthesis: Tetrahedron Lett., 39, 7393 (1998); 40, 7279 (1999). Photolysis of cycloalkanols in the presence of cesium carbonate affords ring-opened ω -iodocarbonyl compounds in good yield: Angew. Chem. Int. Ed., 40, 3389 (2001).
• Photochemical oxidations with the reagent have been reported, e.g. cleavage of 1,2-diols to aldehydes, and oxidation of alcohols to aldehydes or ketones: Chem. Eur. J., 10, 4206 (2004).
• For a brief review on uses of the reagent in synthesis, see: Synlett, 1679 (1999).