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Synlett 2000; 2000(9): 1369
DOI: 10.1055/s-2000-7157
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n-Propane Phosphonic Acid Anhydride - A Condensation Reagent

Michaela Schwarz*
  • *Schering Aktiengesellschaft, Analytik Wirkstoffproduktion, Postfach 1540, D-59179 Bergkamen; Fax +49 (0)23 07/65 22 93; E-mail: michaela.schwarz@schering.de
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Publication History

Publication Date:
31 December 2000 (online)

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n-Propane phosphonic acid anhydride (PPAA) (3) was first used as a condensation reagent in peptide synthesis in 1980 by H. Wissmann and is steadily gaining importance in organic synthesis, e. g. in the synthesis of polyamides or flame-resistant epoxy resins. The anhydride 3 can be prepared from propane phosphonic dichloride and water or is commercially available in solutions of DMF or of ethyl acetate. Application of PPAA in synthesis does not afford any in water insoluble by-products which may be advantageous in laboratory preparations but is of major significance in technical scale productions. According to toxicological studies PPAA is relatively nontoxic compared to other condensation reagents such as DCC or ethylmethyl phosphonic acid anhydride.