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Synlett 2004(9): 1651-1652  
DOI: 10.1055/s-2004-829542
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© Georg Thieme Verlag Stuttgart · New York

Phenyl Dichlorophosphate - A Versatile Reagent

A. K. Adak*
Senior Research Fellow, Department of Chemistry, Bengal ­Engineering College (Deemed University), Howrah-711 103, India
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Publication History

Publication Date:
01 July 2004 (online)

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Introduction

Among several phosphorus acid chlorides described for use in organic synthesis, phenyl dichlorophosphate ­(PDCP, 1) has received added interest due to its powerful phosphorylating nature. The activity of PDCP compared to other chlorophosphate esters was shown to be superior. Phenyl dichlorophosphate is regarded as the most widely used reagent for the preparation of symmetrical phosphate diesters. [1] Other important PDCP-derived phosphorylating agents, e.g. phenylphosphoro di-(1-imidazolidate), 2-phenyl-bis-triazoloylphosphate have been used in peptide synthesis. [2]

Phenyl dichlorophosphate (1) is conveniently prepared by reaction of phosphorus oxychloride with anhydrous ­powdered sodium phenoxide. [3] The precipitated sodium chloride is filtered off and excess phosphorus oxychloride is removed under reduced pressure. The crude oil is ­distilled in a vigreux column and the fraction having the boiling point 103-106 °C (9 mmHg) is collected for chemical reactions.