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Dithiofluorescein

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Dithiofluorescein
Names
IUPAC name 3′,6′-Bis(sulfanyl)spiro-1-one
Other names
    • 3′,6′-Dimercaptofluoran
    • 3′,6′-Dimercaptospiroxanthen]-3-one
    • 3′,6′-Dimercapto-3H-spiro-3-one
    • Thiofluorescein
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 246-830-9
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H12O3S2/c21-19-13-3-1-2-4-14(13)20(23-19)15-7-5-11(24)9-17(15)22-18-10-12(25)6-8-16(18)20/h1-10,24-25HKey: QOMSORNLFVSVPW-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C=C4)S)OC5=C3C=CC(=C5)S
Properties
Chemical formula C20H12O3S2
Molar mass 364.43 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dithiofluorescein (sometimes generically called thiofluorescein) is a complexometric indicator used in analytical chemistry. It changes from blue to colorless when it binds to mercury(2+) ions. It thus can indicate the endpoint in the titration of thiols using o-hydroxymercuribenzoic acid or its sodium salt. The reagent can be immobilized t in a polymer on a fiber optic, which might allow development of a detector for sulfide ions in a flow cell. Unlike fluorescein and other related fluoran dyes that have oxygen substituents on the benzene rings, dithiofluorescein, which has sulfur substituents, is not fluorescent.

References

  1. Wroński, Mieczysław (1966). "Determination of thiol esters with o-hydroxymercuribenzoic acid". Analyst. 19 (2): 745–746. Bibcode:1966Ana....91..745W. doi:10.1039/AN9669100745.
  2. Wroński, Mieczysław (1977). "Analytical applications of o-hydroxymercuribenzoic acid, dithiofluorescein and mercurated fluorescein". Talanta. 24 (6): 347–354. doi:10.1016/0039-9140(77)80019-2. PMID 18962100.
  3. Chromý, V.; Svoboda, V. (1963). "The determination of thiomalic acid". Talanta. 10 (10): 1109–1111. doi:10.1016/0039-9140(63)80152-6.
  4. Narayanaswamy, Ramaier; Sevilla, Fortunato III (1986). "Flow cell studies with immobilised reagents for the development of an optical fibre sulphide sensor". Analyst. 111 (9): 1085. Bibcode:1986Ana...111.1085N. doi:10.1039/AN9861101085.
  5. Sauer, Markus; Hofkens, Johan; Enderlein, Jörg (2011). "2.2. Organic Fluorophores". Handbook of Fluorescence Spectroscopy and Imaging: From Ensemble to Single Molecules. Wiley. pp. 35–38. ISBN 978-3-527-31669-4.
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