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Bis(pyridine)iodonium tetrafluoroborate, 97%, Thermo Scientific Chemicals
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Catalog number L19385.MD
also known as L19385-MD
Price (USD)/ Each
31.60
-
Quantity:
250 mg
Price (USD)/ Each
31.60
Bis(pyridine)iodonium tetrafluoroborate, 97%, Thermo Scientific Chemicals
Catalog numberL19385.MD
Price (USD)/ Each
31.60
-
Chemical Identifiers
CAS15656-28-7
IUPAC Namebis(pyridin-1-ium-1-yl)iodanuide; tetrafluoroboranuide
Molecular FormulaC10H10BF4IN2
InChI KeyBMDSRCBKJZCUBH-UHFFFAOYSA-N
SMILESF[B-](F)(F)F.[I-]([N+]1=CC=CC=C1)[N+]1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to yellow or cream to pale brown
Elemental Analysis(Carbon, C) : 31.33 - 33.26% (theory 32.30%)
Elemental Analysis(Nitrogen, N) : 7.31 - 7.76% (theory 7.53%)
Identification (FTIR)Conforms
Proton NMRConforms to structure
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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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Hydrolyzes in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.
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.
Solubility
Hydrolyzes in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.
RUO – Research Use Only
General 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).