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

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Synonym(s):
2,4,6-Tri-p-anisylpyrylium (TAP) fluoroborate
Empirical Formula (Hill Notation):
C26H23BF4O4
CAS Number:
Molecular Weight:
486.26

form

powder

Quality Level

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

mp

346-351 °C

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-]

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.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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


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Electron?Transfer?Induced Diels?Alder Reactions of Indole and Exocyclic Dienes: Synthesis and Quantum?Chemical Studies.
Haberl U, et al.
Chemistry?A European Journal , 5(10), 2859-2865 (1999)
Synthesis of cyclobutane lignans via an organic single electron oxidant?electron relay system.
Riener M and Nicewicz D A
Chemical Science, 4(6), 2625-2629 (2013)
Christo S Sevov et al.
The Journal of organic chemistry, 73(20), 7909-7915 (2008-09-13)
Electron transfer catalysis is an effective method for the acceleration of Diels-Alder reactions between two substrates of similar electron density. The dependence of the selectivity of the Diels-Alder reaction between (R)-alpha-phellandrene and 4-methoxystyrene catalyzed by photoinduced electron transfer with tris(4-methoxyphenyl)

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