Juni 09, 2024Ethyl dichlorophosphate – preparation and application
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Ethyl dichlorophosphate [1498-51-7] or ethyl phosphorodichloridate is a colorless oily liquid with the boiling point of 58-62 °C/10 mmHg.[1] It is strongly irritating to skin and very toxic by ingestion, inhalation, or by skin absorption due to the inhibition of acetylcholinesterase (IC50 400 nm).[2]
It can be easily prepared from phosphoryl chloride by treatment with 1 equivalent of ethanol in the presence of triethylamine.[3]
Application of Ethyl dichlorophosphate:
It is a highly reactive electrophile suitable for important nucleophilic additions, it can be used in preparation of various nucleoside phosphate and phosphonate prodrugs.[4] It was recently used as a starting material in the synthesis of phosphinanes and azaphosphinanes as potent and selective inhibitors of activated thrombin-activatable fibrinolysis inhibitor (TAFIa) as a promising therapeutic option to treat patients with pulmonary embolism or ischemic stroke by accelerating blood vessel recanalization and improving patient outcome.[5]
Product categorization (Chemical groups):
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[2] Y. Segall, G. B. Quistad, S. E. Sparks, J. E. Casida Chem. Res. Toxicol. 2003, 16 (3), 350. doi:10.1021/tx020094l
[3] S. Jones, D. Selitsianos Tetrahedron Asymmetry, 2005, 16 (18), 3128. doi:10.1016/j.tetasy.2005.08.025
[4] U. Pradere, E. C. Garnier-Amblard, S. J. Coats, F. Amblard, R. F. Schinazi Chem. Rev. 2014, 114, 9154. doi:10.1021/cr5002035
[5] A. P. Schaffner, P. Sansilvestri-Morel, N. Despaux, E. Ruano, T. Persigand, A. Rupin, P. Mennecier, M. O. Vallez, E. Raimbaud, P. Desos, P. Gloanec J. Med. Chem. 2021, 64 (7), 3897. doi:10.1021/acs.jmedchem.0c02072