4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH): A new chromophoric reagent for quantitative monitoring of solid-phase aldehydes

Simon K. Shannon, George Barany

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15 Scopus citations


A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N- dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (ε301nm = 7800 M-1 cm-1) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

Original languageEnglish (US)
Pages (from-to)4586-4594
Number of pages9
JournalJournal of Organic Chemistry
Issue number14
StatePublished - Jul 9 2004


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