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906719

Pyrylium tetrafluoroborate

≥95%

Synonym(s):

Pyry-BF4

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About This Item

Empirical Formula (Hill Notation):
C5H5BF4O
CAS Number:
80279-50-1
Molecular Weight:
167.90
MDL number:
MFCD32857267
UNSPSC Code:
12352107
NACRES:
NA.22
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assay

≥95%

form

powder

storage temp.

2-8°C

SMILES string

[B-](F)(F)(F)F.[o+]1ccccc1

InChI

1S/C5H5O.BF4/c1-2-4-6-5-3-1;2-1(3,4)5/h1-5H;/q+1;-1

InChI key

SJNICXIZTGPXAU-UHFFFAOYSA-N

Application

Pyrylium tetrafluoroborate is used for the functionalization of heterocyclic amines, activating them for nucleophilic substitution. As demonstrated by the Cornella lab, the intermediate pyridinium salts can react with a vast array of nucelophiles to form new C-N, C-O, and C-S bonds, making pyrylium tetrafluoroborate a valuable reagent for late-stage functionalization.

Other Notes

Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by PyryBF4

Synthesis of Sulfonyl Fluorides from Sulfonamides

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000237945
0000187683
0000237945
0000187683
0000184049

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Related Content

Cornella Group – Professor Product Portal

The main focus of the Cornella research group is the development of rapid, practical and efficient methodologies for organic synthesis. In addition to efficiency and practicality, the group is highly interested in discovering new reactivity with the aim of unveiling novel transformations. More specifically, on the fundamental understanding and application of catalytic processes and the development of simple reagents. These two approaches have enormous potential and impact across the chemical sciences.

Daniel Moser et al.
Angewandte Chemie (International ed. in English), 57(34), 11035-11039 (2018-07-04)
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4 ) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C-N bond for nucleophilic aromatic substitution. More than 60 examples for the

Global Trade Item Number

SKUGTIN
906719-1G04054839936838
906719-5G04054839936845