Bis(pyridine)iodonium tetrafluoroborate

• Catalog No.: L19385
• CAS Number: 15656-28-7
• M. F.: C10H10BF4IN2++
• M. W.: 371.9088828
• Purity: 97%

SYNONYMS

• Title: 双(吡啶)四氟硼化碘
• 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

DATABASE IDS

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

PROPERTIES

• Purity: 97%
• Melting Point: ca 160°C dec.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P280G-P305+P351+P338
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture & Light Sensitive
• TSCA Listed: 否

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).