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531634

Sigma-Aldrich

Bis(pyridine)iodonium tetrafluoroborate

Synonym(s):

Barluenga reagent

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About This Item

Empirical Formula (Hill Notation):
C10H10BF4IN2
CAS Number:
15656-28-7
Molecular Weight:
371.91
MDL number:
MFCD03703393
UNSPSC Code:
12352005
PubChem Substance ID:
24877831
NACRES:
NA.22

reaction suitability

reagent type: oxidant

mp

137-141 °C (lit.)

storage temp.

2-8°C

SMILES string

[I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2

InChI

1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1

InChI key

JBVUIHBKNVHCKK-UHFFFAOYSA-N

General description

Bis(pyridine)iodonium Tetrafluoroborate (Barluenga′s reagent) is a mild iodinating and oxidizing reagent capable of selectively reacting with a wide range of unsaturated substrates and tolerates a variety of functional groups.

Application

Bis(pyridine)iodonium Tetrafluoroborate reacts with acetonides derived from simple terpenes to accomplish selective iodofunctionalization with excellent regio- and diastereofacial control. It has been used as a reactant involved in:

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Campos, P. J. et al
Tetrahedron Letters, 38, 8397-8397 (1997)
José Barluenga et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(17), 4206-4213 (2004-09-08)
The use of bis(pyridine)iodonium tetrafluoroborate (IPy(2)BF(4)) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions.

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