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Thioindigo is an organosulfur compound that is used to dye polyester fabric. A synthetic dye, thioindigo is related to the plant-derived dye Indigo dye, replacing two NH groups with two sulfur atoms to create a shade of pink.
Thioindigo is generated by the alkylation of the sulfur in thiosalicylic acid with chloroacetic acid. The resulting thioether cyclizes to 2-hydroxythianaphthene, which is easily converted to thioindigo.Elmar Steingruber "Indigo and Indigo Colorants" in Ullmann's Encyclopedia of Industrial Chemistry, 2004, Wiley-VCH, Weinheim. The related compound 4,7,4',7'-tetrachlorothioindigo, also a commercially important dye (Pigment Red 88), can be prepared by chlorination of thioindigo.
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