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Sigma-Aldrich

5-Vinylthianthrenium tetrafluoroborate

≥95%

Synonym(s):

Vinyl-TT

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About This Item

Empirical Formula (Hill Notation):
C14H11BF4S2
CAS Number:
2703016-98-0
Molecular Weight:
330.17

Quality Level

100

assay

≥95%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

110-112 °C

storage temp.

−20°C

SMILES string

[F-][B+3]([F-])([F-])[F-].S1C=2C=CC=CC2[S+](C=C)C=3C=CC=CC13

InChI

1S/C14H11S2.BF4/c1-2-16-13-9-5-3-7-11(13)15-12-8-4-6-10-14(12)16;2-1(3,4)5/h2-10H,1H2;/q+1;-1

InChI key

FXHBWPNFHMRFKM-UHFFFAOYSA-N

Related Categories

Application

5-Vinylthianthrenium tetrafluoroborate is a crystalline, shelf-stable vinylating reagent developed by the Ritter Lab. Despite the great functionality of the vinyl group for diversification of target compounds, the selective installation of this moeity has remained challenging. 5-Vinylthianthrenium tetrafluoroborate can perform this otherwise challenging transformation with a broad scope of substrate, including the N-vinylation of heterocycles, vinylation of aryl boronic acids, and the annulation of cyclic and heterocyclic substrates. Additionally, this reagent can be used to enable palladium catalyzed cross-coupling reactions. The functionality of 5-vinylthianthrenium tetrafluoroborate enables the usage of vinyl groups as a versatile tool for further functionalization of many substrates and is a functional tool for many snythetic pathways.

Other Notes

Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
Fabio Julia, et al
Journal of the American Chemical Society, 143, 33, 12992?12998-12992?12998 (2021)

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