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900692

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

powder

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
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Product Name

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

form

powder

Quality Level

100

reaction suitability

reagent type: catalyst
core: pyrylium
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-]

InChI

1S/C26H23O4.BF3.FH/c1-27-22-10-4-18(5-11-22)21-16-25(19-6-12-23(28-2)13-7-19)30-26(17-21)20-8-14-24(29-3)15-9-20;2-1(3)4;/h4-17H,1-3H3;;1H/q+1;;/p-1

InChI key

BYUPZXIJGVBLGP-UHFFFAOYSA-M

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

signalword

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

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
MKCM8305
MKCC8338

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Related Content

Nicewicz Group – Prof. Product Portal

Nicewicz lab focuses on reactive cation radical species for selective reactions, advancing synthesis methodologies for various functional groups.

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)

Global Trade Item Number

SKUGTIN
900692-250MG04061833259290
900692-10MG04061833259283