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Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions
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Abstract
The synthesis of dyes has long been a popular topic in organic chemistry laboratory experiments because it allows students to see first hand that reactions learned in class can be used to make compounds with useful applications. In this experiment electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B). These dyes can be readily synthesized using equipment found in most common second-year organic labs. Hydroscopic Lewis acids, which are often troublesome to use in a typical lab setup, are avoided. The dyes synthesized in this experiment can each be completed in one four-hour laboratory session. Approximately 30 minutes in a subsequent period will be required for UV–vis analysis, and the student samples give UV–vis spectra that match commercially available dye samples.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Acids / BasesCiting Articles
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This article has been cited by 2 ACS Journal articles (2 most recent appear below).
UV–Visible Spectrometers: Versatile Instruments across the Chemistry Curriculum
Demetra A. C. Czegan and Diana K. HooverJournal of Chemical Education2012 Article ASAPUV–Visible Spectrometers: Versatile Instruments across the Chemistry Curriculum
Demetra A. C. Czegan and Diana K. HooverJournal of Chemical Education2012 Article ASAPThis article describes a wide range of commercially available UV–vis spectrometers, with particular emphasis on educational models, and how this technique can be included in all aspects of the chemistry curriculum. Portable instrumentation and new ...
Molecular Models of Dyes
William F. ColemanJournal of Chemical Education2007 84 (11), 1798Molecular Models of Dyes
William F. ColemanJournal of Chemical Education2007 84 (11), 1798The JCE Featured Molecules for this month include the triarylmethane and xanthene dyes fluorescein, erythrosin B, thymolphthalein, and rhodamine B.
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- Received: August 03, 2009
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