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MedKoo Cat#: 585259 | Name: Thioindigo
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thioindigo is an organosulfur compound that is used to dye polyester fabric.

Chemical Structure

Thioindigo
Thioindigo
CAS#522-75-8

Theoretical Analysis

MedKoo Cat#: 585259

Name: Thioindigo

CAS#: 522-75-8

Chemical Formula: C16H8O2S2

Exact Mass: 295.9966

Molecular Weight: 296.36

Elemental Analysis: C, 64.85; H, 2.72; O, 10.80; S, 21.64

Price and Availability

Size Price Availability Quantity
25mg USD 255.00
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Related CAS #
No Data
Synonym
Thioindigo
IUPAC/Chemical Name
Benzo(b)thiophen-3(2H)-one, 2-(3-oxobenzo(b)thien-2(3H)-ylidene)-
InChi Key
JOUDBUYBGJYFFP-FOCLMDBBSA-N
InChi Code
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+
SMILES Code
O=C1C2=CC=CC=C2S/C1=C3C(C4=CC=CC=C4S\3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 296.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.