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900685

2,4,6-Tri(p-tolyl)pyrylium tetrafluoroborate salt

≥95%, powder

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About This Item

Empirical Formula (Hill Notation):
C26H23BF4O
CAS Number:
2713-21-5
Molecular Weight:
438.26
MDL number:
MFCD00972530
UNSPSC Code:
12161600
NACRES:
NA.22
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Product Name

2,4,6-Tri(p-tolyl)pyrylium tetrafluoroborate salt, ≥95%

Quality Level

100

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

mp

298-303 °C

SMILES string

[B-](F)(F)(F)F.[o+]1c(cc(cc1c4ccc(cc4)C)c3ccc(cc3)C)c2ccc(cc2)C

InChI

1S/C26H23O.BF4/c1-18-4-10-21(11-5-18)24-16-25(22-12-6-19(2)7-13-22)27-26(17-24)23-14-8-20(3)9-15-23;2-1(3,4)5/h4-17H,1-3H3;/q+1;-1

InChI key

BWOXOWBZXLPNEN-UHFFFAOYSA-N

Application

Excitable by blue LEDs, this photocatalyst was reported by the Nicewicz laboratory for catalysis of O-aryl carbamothioates to S-aryl carbamothioates at ambient temperatures, an improvement from the elevated reaction temperatures traditionally needed in the Newman-Kwart rearrangment or palladium catalysis. Effective for scale-up or flow chemistry, this triarylpyrylium salt provides convenient access to thiophenols from phenols.
It can also catalyze visible light-initiated, living cationic polymerization of 4-methoxystyrene with methanol under metal-free conditions.

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

Other Notes

Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis
Cycloaddition Reactions Initiated by Photochemically Excited Pyrylium Salts

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Related Content

Photoredox Catalysis

Photoredox catalysis utilizes photocatalysts in the presence of visible light to form an array of synthetic transformations including, but not limited to, cross-coupling, C-H functionalization, alkene and arene functionalization, and trifluoromethylation.

Nicewicz Group – Prof. Product Portal

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

Visible light photoinitiated metal-free living cationic polymerization of 4-methoxystyrene.
Perkowski A J, et al.
Journal of the American Chemical Society, 137(24), 7580-7583 (2015)

Global Trade Item Number

SKUGTIN
900685-250MG04061833259276