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Key Documents

900692

Sigma-Aldrich

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H23BF4O4
CAS Number:
Molecular Weight:
486.26
UNSPSC Code:
12161600
NACRES:
NA.22

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


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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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)

Related Content

The Nicewicz lab is focused on the discovery of new and powerful reaction methodologies that proceed via the intermediacy of highly reactive cation radical species. Included in these transformations are anti-Markovnikov selective additions of amines, alcohols, carboxylic acids, amides and mineral acids to alkenes.

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