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900692

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

powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C26H23BF4O4
Numéro CAS:
580-34-7
Poids moléculaire :
486.26
UNSPSC Code:
12161600
NACRES:
NA.22
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Nom du produit

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

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)
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.

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

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Contenu apparenté

Nicewicz Group – Prof. Product Portal

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

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)

Numéro d'article de commerce international

RéférenceGTIN
900692-250MG04061833259290
900692-10MG04061833259283