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Scalable Regioselective Synthesis of Rhodamine Dyes

Stephen J Dwight, Sergiy Levin

Org Lett. 2016 Oct 21;18(20):5316-5319.

PMID: 27704864

Abstract:

A one-step, operationally simple protocol for the synthesis of isomerically pure rhodamine dyes from phthalaldehydic acids is reported. Using a mixture of 2,2,2-trifluoroethanol and water as reaction media allows for clean and efficient formation of various rhodamines as a single isomer. This method was successfully applied to the synthesis of several isomerically pure rhodamines, including 6-carboxytetramethylrhodamine and 6-carboxy-X-rhodamine (6-CXR) on gram scale. A simple, one-step, Pd-catalyzed hydroxycarbonylation approach to phthalaldehydic acids from appropriately substituted dihalobenzadehydes is also described.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP91809675 6-Carboxytetramethylrhodamine 6-Carboxytetramethylrhodamine 91809-67-5 Price
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