925446

5-Vinylthianthrenium tetrafluoroborate

≥95%

• Synonym(s): Vinyl-TT
• Empirical Formula (Hill Notation): C₁₄H₁₁BF₄S₂
• CAS Number: 2703016-98-0
• Molecular Weight: 330.17
• UNSPSC Code: 12352108
• NACRES: NA.22

Properties

• 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

Description

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable