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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:
580-34-7
Molecular Weight:
486.26
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder

Quality Level

100

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)

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

Pictograms

Exclamation mark
GHS07

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

JAN Code

900692-250MG:4548174014271
900692-10MG:4548174014264
900692-VAR:
900692-BULK:

Certificates of Analysis (COA)

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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)
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)
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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