Bis(pyridine)iodonium tetrafluoroborate

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Bis(pyridine)iodonium tetrafluoroborate Basic information
Product Name:Bis(pyridine)iodonium tetrafluoroborate
Synonyms:BIS(PYRIDINE)IODONIUM(1)TETRAFLUOROBORATE;BARLUENGAS REAGENT IPY2BF4 BIS(PYRIDINE)IODONIUM(I) ETRAFLUOROBORATE;Iodanium pyridine tetrafluoroborate;BarluengaReagentIpy2Bf4;Bis(pyridine)iodonium tetrafluoroborate,97%;Bis(pyridine)iodonium tetrafluoroborate≥ 97% (NMR);BIS(PYRIDINE)IODONIUM (I) TETRAFLUOROBORATE;BIS(PYRIDINE)IODONIUM TETRAFLUOROBORATE
CAS:15656-28-7
MF:C10H10BF4IN2
MW:371.91
EINECS:628-405-3
Product Categories:Hypervalent Iodine;Oxidation;Synthetic Reagents
Mol File:15656-28-7.mol
Bis(pyridine)iodonium tetrafluoroborate Structure
Bis(pyridine)iodonium tetrafluoroborate Chemical Properties
Melting point 137-141 °C (lit.)
storage temp. 2-8°C
solubility sol CH2Cl2, DMSO, MeCN, pyridine, DMF; modestly sol CHCl3; insol ether, THF, hexane
form Powder
color Yellow
Water Solubility Hydrolyzes in water.
Sensitive Moisture & Light Sensitive
Merck 14,1302
BRN 4284739
InChI1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1
InChIKeyJBVUIHBKNVHCKK-UHFFFAOYSA-N
SMILES[I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2
CAS DataBase Reference15656-28-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR 1759
WGK Germany 3
Hazard Note Toxic/Irritant
HazardClass MOISTURE SENSITIVE, KEEP COLD, LIGHT SENSITIVE
PackingGroup II
HS Code 29333990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
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Bis(pyridine)iodonium tetrafluoroborate Usage And Synthesis
DescriptionBis(pyridine)iodonium tetrafluoroborate is iodinating agent for the selective functionalization of unsaturated compounds; can also mediate C-C bond formation.
PreparationBis(pyridine)iodonium tetrafluoroborate is prepared by the reaction of HgO/HBF4-SiO2 with iodine and pyridine in dry CH2Cl2 at rt. Solids are filtered off, and the reagent is isolated by precipitation from CH2Cl2 solution by addition  of cold ether, repeating the operation several times until a negative test for mercury(II) is obtained (i.e. absence of precipitation of mercury by treatment of an aliquot with NaBH4/NaOH).
Chemical PropertiesYellow powder
UsesBis(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.
reaction suitabilityreagent type: oxidant
storageBis(pyridine)iodonium tetrafluoroborate can be safely stored under a nitrogen atmosphere (in the dark at 4 °C)  for long periods of time (up to 3 months has been observed) without changing either properties or physical  appearance.
Purification Methodsrecrystallization from CH2Cl2-CHCl3 (white solid)
Bis(pyridine)iodonium tetrafluoroborate Preparation Products And Raw materials
Raw materialsPyridine-->Iodine-->Fluoroboric acid-->Silica gel-->Mercuric Oxide
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