Structure via PubChem · Public domain (PubChem)
thioindigo
Sign in to saveThioindigo 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 to create a shade of pink.
Chemical data
- Formula
- C16H8O2S2
- Molecular weight
- 296.4 g/mol
- IUPAC name
- (2E)-2-(3-oxo-1-benzothiophen-2-ylidene)-1-benzothiophen-3-one
- SMILES
- C1=CC=C2C(=C1)C(=O)/C(=C\3/C(=O)C4=CC=CC=C4S3)/S2
- InChIKey
- JOUDBUYBGJYFFP-FOCLMDBBSA-N
- XLogP
- 4.1
- Polar surface area
- 84.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 295.996571
Show 6 more facts
- Commons category
- Thioindigo
- chemical formula
- C₁₆H₈O₂S₂
- canonical SMILES
- C1=CC=C2C(=C1)C(=O)C(=C3C(=O)C4=CC=CC=C4S3)S2
- isomeric SMILES
- C1=CC=C2C(=C1)C(=O)/C(=C\3/C(=O)C4=CC=CC=C4S3)/S2
- described by source
- Brockhaus and Efron Encyclopedic Dictionary
- melting point
- 359
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- 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 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. The related compound 4,7,4',7'-tetrachlorothioindigo, also a commercially important dye (Pigment Red 88), can be prepared by chlorination of thioindigo.
Excerpted from Wikipedia’s “thioindigo” article, available under the CC BY-SA 4.0 licence.