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900692 Sigma-Aldrich

2,4,6-Tris(4-methoxyphenyl)pyrylium tetrafluoroborate

≥95%

Synonym: 2,4,6-Tri-p-anisylpyrylium (TAP) fluoroborate

  • CAS Number 580-34-7

  • Empirical Formula (Hill Notation) C26H23BF4O4

  • Molecular Weight 486.26

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Other Catalysts, Photocatalysis
Quality Level   100
assay   ≥95%
form   powder
mp   346-351 °C
reaction suitability   reagent type: catalyst
reaction type: Photocatalysis
SMILES string   COC(C=C1)=CC=C1C2=[O+]C(C3=CC=C(OC)C=C3)=CC(C4=CC=C(OC)C=C4)=C2.FB(F)F.[F-]

Description

Application

2,4,6-Tris(4-methoxyphenyl)pyrylium tetrafluoroborate can be used to catalyze the stereoselective synthesis of C2-symmetric cyclobutane alkene dimers via photo-induced electron transfer. This method can be employed for the total synthesis of lignans such as magnosalin, endiandrin A and pellucidin A. It can also catalyze photoinduced electron transfer (PET) to initiate radical-cation Diels-Alder reactions.

Triarylpyrylium salt used as a photosensitizer in photocatalysis and polymerization. This was previously sold under catalog number S921874.

Packaging

10, 250 mg in glass insert

Other Notes

David Nicewicz photoredox catalysis
Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
Metal-Free Ring-Opening Metathesis Polymerization
Cationic Polymerization of Vinyl Ethers Controlled by Visible Light
Electron-Transfer-Induced Diels ± Alder Reactions of Indole and Exocyclic Dienes: Synthesis and Quantum-Chemical Studies

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

David Nicewicz Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents David Nicewicz Group - Professor Product Portal
Keywords: Addition reactions, Catalysis, Cycloadditions, Hydroaminations, Infrared spectroscopy, Oxidations

Peer-Reviewed Papers
15

References

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