Thioindigo

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Thioindigo
Skeletal formula of thioindigo
Ball-and-stick model of the thioindigo molecule
Names
IUPAC name
2-(3-Oxo-1-benzothiophen-2(3H)-ylidene)-1-benzothiophen-3(2H)-one
Other names
DyStar, C.I. Vat Red 41, C.I. 73 300
Identifiers
522-75-8 YesY
ChemSpider 4527286 N
Jmol-3D images Image
PubChem 3033973
Properties
C16H8O2S2
Molar mass 296.36 g·mol−1
Appearance Red solid
Melting point 280 °C (536 °F; 553 K)
Insoluble
Solubility in ethanol, xylene Soluble[vague]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Thioindigo is an organosulfur compound that is used to dye polyester fabric. A synthetic dye, thioindigo is related to the plant-derived dye indigo, replacing two NH groups with two sulfur atoms.

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.[1] The related compound 4,7,4',7'-tetrachlorothioindigo, also a commercially important dye, can be prepared by chlorination of thioindigo.

References[edit]

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