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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4
Jose Barluenga et al.
The Journal of Organic Chemistry, 68(17), 6583-6586 (2003)
José Barluenga et al.
Organic letters, 5(22), 4121-4123 (2003-10-24)
[reaction: see text]. Iodonium ions, o-alkynyl-substituted carbonyl compounds, and alkynes react to give 1-iodonaphthalene derivatives featuring interesting substitution patterns. The reaction with alkenes instead of acetylenes affords related naphthyl ketone derivatives. These two metal-free processes are conducted at room temperature
José Barluenga et al.
Journal of the American Chemical Society, 125(30), 9028-9029 (2004-09-17)
Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and
Cyclization of Carbonyl Groups onto Alkynes upon Reaction with IPy2BF4 and Their Trapping with Nucleophiles:? A Versatile Trigger for Assembling Oxygen Heterocycles
Jose Barluenga et al.
Journal of the American Chemical Society, 125(30), 9028-9029 (2003)
?-Iodination of enaminones with bis(pyridine)iodonium(I) tetrafluoroborate
Campos, P. J. et al
Tetrahedron Letters, 38(48), 8397-8400 (1997)
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