531634
Bis(pyridine)iodonium tetrafluoroborate
Sinónimos:
Barluenga reagent
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1 G
$66.22
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1 G
$66.22
About This Item
Fórmula empírica (notación de Hill):
C10H10BF4IN2
Número de CAS:
Peso molecular:
371.91
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Productos recomendados
Quality Level
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
Application
Bis(pyridine)iodonium Tetrafluoroborate reacts with acetonides derived from simple terpenes to accomplish selective iodofunctionalization with excellent regio- and diastereofacial control.[3] It has been used as a reactant involved in:
- Synthesis of substituted naphthalenes[4] and oxygen containing heterocycles[5] from 2-alkynyl-substituted benzaldehydes.
- Synthesis of tetracyclic tetrahydrofurans[6]
Applications for Bis(pyridine)iodonium Tetrafluoroborate
signalword
Warning
hcodes
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
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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
Discovery of New Tetracyclic Tetrahydrofuran Derivatives as Potential Broad-Spectrum Psychotropic Agents
Fernandez J. et al.
Journal of Medicinal Chemistry, 48(6), 1709-1712 (2005)
Regioselective synthesis of substituted naphthalenes: a novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes
Jose Barluenga et al.
Organic Letters, 5(22), 4121-4123 (2003)
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)
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