925446
5-Vinylthianthrenium tetrafluoroborate
≥95%
Synonym(s):
Vinyl-TT
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About This Item
Empirical Formula (Hill Notation):
C14H11BF4S2
CAS Number:
Molecular Weight:
330.17
MDL number:
UNSPSC Code:
12352108
NACRES:
NA.22
Product Name
5-Vinylthianthrenium tetrafluoroborate, ≥95%
assay
≥95%
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
form
powder
reaction suitability
reaction type: C-C Bond Formation
mp
110-112 °C
functional group
thioether
storage temp.
−20°C
Quality Level
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation
Hartmann P, et al.
Nature Chemistry, 16, 380-388 (2024)
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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