Thioindigo

For research use only. Not for therapeutic Use.

  • CAT Number: I037232
  • CAS Number: 522-75-8
  • Molecular Formula: C16H8O2S2
  • Molecular Weight: 296.36
  • Purity: 98%
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Thioindigo (Cat No.:I037232) is an organic compound that is part of the indigo dye family. It is derived from indigo by replacing one of the oxygen atoms with a sulfur atom. Thioindigo is known for its intense blue color and has been used as a dye in various applications, including textiles, inks, and paints. It exhibits good color fastness and has been valued for its ability to retain its vibrant blue hue over time. Thioindigo’s chemical structure and properties make it a versatile compound in the field of colorants and dye chemistry.


Catalog Number I037232
CAS Number 522-75-8
Synonyms

Thioindigo

Molecular Formula C16H8O2S2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name Benzo(b)thiophen-3(2H)-one, 2-(3-oxobenzo(b)thien-2(3H)-ylidene)-
InChI InChI=1S/C16H8O2S2/c17-13-9-5-1-3-7-11(9)19-15(13)16-14(18)10-6-2-4-8-12(10)20-16/h1-8H/b16-15+
InChIKey JOUDBUYBGJYFFP-FOCLMDBBSA-N
SMILES O=C1C2=CC=CC=C2S/C1=C3C(C4=CC=CC=C4S3)=O
Reference

1: Boice G, Patrick BO, McDonald R, Bohne C, Hicks R. Synthesis and photophysics of thioindigo diimines and related compounds. J Org Chem. 2014 Oct 3;79(19):9196-205. doi: 10.1021/jo501630f. Epub 2014 Sep 23. PubMed PMID: 25198938.
2: Ibrahim M, El-Nahass MM, Kamel MA, El-Barbary AA, Wagner BD, El-Mansy MA. On the spectroscopic analyses of thioindigo dye. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Sep;113:332-6. doi: 10.1016/j.saa.2013.05.014. Epub 2013 May 17. PubMed PMID: 23743038.
3: Lemieux RP. Photoswitching of ferroelectric liquid crystals using chiral thioindigo dopants: The development of a photochemical switch hitter. Chem Rec. 2004;3(5):288-95. PubMed PMID: 14762829.
4: Alvarado M Jr, Chianelli RC, Arrowood RM. Computational study of the structure of a sepiolite/thioindigo mayan pigment. Bioinorg Chem Appl. 2012;2012:672562. doi: 10.1155/2012/672562. Epub 2012 Nov 1. PubMed PMID: 23193386; PubMed Central PMCID: PMC3501801.
5: Vlahakis JZ, Wand MD, Lemieux RP. Photoinduced polarization inversion in a ferroelectric liquid crystal using an ambidextrous chiral thioindigo dopant. J Am Chem Soc. 2003 Jun 11;125(23):6862-3. PubMed PMID: 12783527.
6: Jacquemin D, Preat J, Wathelet V, Fontaine M, Perpète EA. Thioindigo dyes: highly accurate visible spectra with TD-DFT. J Am Chem Soc. 2006 Feb 15;128(6):2072-83. PubMed PMID: 16464110.
7: Dittmann M, Graupner FF, Maerz B, Oesterling S, de Vivie-Riedle R, Zinth W, Engelhard M, Lüttke W. Photostability of 4,4′-dihydroxythioindigo, a mimetic of indigo. Angew Chem Int Ed Engl. 2014 Jan 7;53(2):591-4. doi: 10.1002/anie.201307016. Epub 2013 Nov 26. PubMed PMID: 24282071.
8: Chatterjee M, Mondal S, Ghosh P, Kaim W, Lahiri GK. Mononuclear and Dinuclear Ruthenium Complexes of cis- and trans-Thioindigo: Geometrical and Electronic Structure Analyses. Inorg Chem. 2018 Oct 1;57(19):12187-12194. doi: 10.1021/acs.inorgchem.8b01829. Epub 2018 Sep 10. PubMed PMID: 30198711.
9: Costa AL, Gomes AC, Pereira RC, Pillinger M, Gonçalves IS, Pineiro M, Seixas de Melo JS. Interactions and Supramolecular Organization of Sulfonated Indigo and Thioindigo Dyes in Layered Hydroxide Hosts. Langmuir. 2018 Jan 9;34(1):453-464. doi: 10.1021/acs.langmuir.7b03735. Epub 2017 Dec 28. PubMed PMID: 29231742.
10: Ross DL. Photochromic Indigoids. III: A Photochromic Element Based on the cis-trans Photoisomerization of a Thioindigo Dye. Appl Opt. 1971 Mar 1;10(3):571-6. doi: 10.1364/AO.10.000571. PubMed PMID: 20094492.
11: Ghelardi E, Degano I, Colombini MP, Mazurek J, Schilling M, Learner T. Py-GC/MS applied to the analysis of synthetic organic pigments: characterization and identification in paint samples. Anal Bioanal Chem. 2015 Feb;407(5):1415-31. doi: 10.1007/s00216-014-8370-y. Epub 2014 Dec 27. PubMed PMID: 25542568.
12: Koeppe B, Römpp F. Reversible Spatial Control in Aqueous Media by Visible Light: A Thioindigo Photoswitch that is Soluble and Operates Efficiently in Water. Chemistry. 2018 Sep 25;24(54):14382-14386. doi: 10.1002/chem.201803675. Epub 2018 Sep 4. PubMed PMID: 30058151.
13: Boice GN, Garakyaraghi S, Patrick BO, Sanz CA, Castellano FN, Hicks RG. Diastereomerically Differentiated Excited State Behavior in Ruthenium(II) Hexafluoroacetylacetonate Complexes of Diphenyl Thioindigo Diimine. Inorg Chem. 2018 Feb 5;57(3):1386-1397. doi: 10.1021/acs.inorgchem.7b02803. Epub 2018 Jan 23. PubMed PMID: 29360353.
14: Baluja G, Franco JM, Murado MA. Interference of phenoxyacetic acid derivatives in the estimation of monochloroacetic acid by the thioindigo method. Arch Environ Contam Toxicol. 1973 Dec;1(4):375-80. PubMed PMID: 4781319.
15: Zavgorodniĭ IV, Vasilenko NM, Osychenko SN. [The characteristics of the health and hygienic conditions of working in the manufacture of thioindigo-based vat dyes]. Gig Tr Prof Zabol. 1992;(2):39-41. Russian. PubMed PMID: 1427303.
16: Polette-Niewold LA, Manciu FS, Torres B, Alvarado M Jr, Chianelli RR. Organic/inorganic complex pigments: ancient colors Maya Blue. J Inorg Biochem. 2007 Nov;101(11-12):1958-73. Epub 2007 Jul 18. PubMed PMID: 17761292.
17: Bressler DC, Fedorak PM. Purification, stability, and mineralization of 3-hydroxy-2- formylbenzothiophene, a metabolite of dibenzothiophene. Appl Environ Microbiol. 2001 Feb;67(2):821-6. PubMed PMID: 11157249; PubMed Central PMCID: PMC92653.
18: Cordes T, Schadendorf T, Priewisch B, Rück-Braun K, Zinth W. The Hammett relationship and reactions in the excited electronic state: hemithioindigo Z/E-photoisomerization. J Phys Chem A. 2008 Jan 31;112(4):581-8. doi: 10.1021/jp077472l. Epub 2008 Jan 5. PubMed PMID: 18177026.
19: Perpète EA, Preat J, André JM, Jacquemin D. An ab initio study of the absorption spectra of indirubin, isoindigo, and related derivatives. J Phys Chem A. 2006 May 4;110(17):5629-35. PubMed PMID: 16640356.
20: Muzzall JM, Cook WL. Mutagenicity test of dyes used in cosmetics with the Salmonella/mammalian-microsome test. Mutat Res. 1979 May;67(1):1-8. PubMed PMID: 379635.

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