Thioindigo

Thioindigo
Identifiers
CAS number 522-75-8 Y=
Properties
Molecular formula C16H8O2S2
Molar mass 296.37
Appearance red solid
Melting point

280 °C, 553 K, 536 °F

Solubility in water polar organic solvents
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thioindigo is an organosulfur compound that is used for dying polyester fabrics. It is related to the more common dye indigo by replacement of two NH groups with sulfur atoms.

It is prepared by S-alkylation of thiosalicylic acid with chloroacetic acid. The resulting thioether cyclizes to 2-hydroxythionaphthene, which dimerizes.[1] The related compound 4,7,4',7'-tetrachlorothioindigo, also a commercially important dye, can be prepared by chlorination of thioindigo.

References

  1. ^ Elmar Steingruber "Indigo and Indigo Colorants" Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a14_149.pub2