thianthrene 5-oxide Chemical Properties

Melting point:

143-143.5 °C

Boiling point:

423.2±15.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder

Appearance

White to off-white Solid

InChI

1S/C12H8OS2/c13-15-11-7-3-1-5-9(11)14-10-6-2-4-8-12(10)15/h1-8H

InChIKey

NYVGTLXTOJKHJN-UHFFFAOYSA-N

SMILES

[S+]1(c2c(cccc2)Sc3c1cccc3)[O-]

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

thianthrene 5-oxide Usage And Synthesis

Uses

Thianthrene S-oxide is a sulfoxide-based thianthrene reagent for late-stage C-H functionalization. Developed by the Ritter Lab, C-H functionalization by thianthrenation proceeds with >99% selectivity and furnishes functionalized arenes serving as synthetic linchpins for further participation in diverse transformations. Nonfluorinated thianthrene S-oxide is best used for all arenes more electron-rich than anisole. For other arenes, the fluorinated TFT S-oxide (903981) was demonstrated as the thanthrenation reagent.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2163, 1956 DOI: 10.1021/ja01591a037
Synthetic Communications, 22, p. 1799, 1992 DOI: 10.1080/00397919208020500

thianthrene 5-oxide(2362-50-7)Related Product Information

• Thianthrene