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Merck
CN

900685

Sigma-Aldrich

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

Key Documents

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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

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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 Code

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
MKCC8337

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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)

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Nicewicz Group – Prof. Product Portal

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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