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15656-28-7 - Bis(pyridine)iodonium tetrafluoroborate, 97% - Barluenga's Reagent - L19385 - Alfa Aesar

L19385 Bis(pyridine)iodonium tetrafluoroborate, 97%

CAS Number
15656-28-7
Synonyms
Barluenga's Reagent

Size Price ($) Quantity Availability
250mg 26.06
1g 54.72
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Bis(pyridine)iodonium tetrafluoroborate, 97%

MDL
MFCD03703393

Chemical Properties

Formula
C10H10BF4IN2
Formula Weight
371.91
Melting point
ca 160° dec.
Sensitivity
Moisture & Light Sensitive
Solubility
Hydrolyzes in water.

Applications

Bis(pyridine)iodonium tetrafluoroborate is used as mild iodinating and oxidizing reagent. It is also useful for selective iodination of free phenolic groups in tyrosine residues during solid-phase synthesis.

Notes

Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.

Literature References

Yoshifumi Maegawa.; Yasutomo Goto.; Shinji Inagaki.; Toyoshi Shimada. A useful procedure for diiodination of carbazoles and subsequent efficient transformation to novel 3,6-bis(triethoxysilyl)carbazoles giving mesoporous materials. Tetrahedron Letters. 2006, 47 (39), 6957-6960.

Benito Alcaide.; Pedro Almendros.; Amparo Luna.; M. Rosario Torres. Divergent Reactivity of 2-Azetidinone-Tethered Allenols with Electrophilic Reagents: Controlled Ring Expansion versus Spirocyclization. Advanced Synthesis & Catalysis. 2010, 352 (4), 621-626.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P280g-P305+P351+P338

Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Other References

Beilstein
4284739
Harmonized Tariff Code
2933.39
TSCA
No

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