Diethyl chlorophosphite acts as a versatile phosphorylating agent for ester and lactone enolates, amines and alkenols. It is used in the synthesis of organophosphates and are considered anticholinesterase agents through observation in studies.
Bilha Fischer and Larisa Sheihet. Diethyl Chlorophosphite:? A Mild Reagent for Efficient Reduction of Nitro Compounds to Amines.J. Org. Chem.1998, 63 (2), 393-395.
George W. Anderson; Alice D. Welcher; Richard W. Young. Diethyl Chlorophosphite as a Reagent for Peptide Syntheses.J. Am. Chem. Soc.1951, 73 (1), 501-502.
Reacts readily with nucleophiles, e.g. amines, alcohols or organometallic species, with the introduction of a phosphorus substituent. The phosphorylation of OH groups has been brought about by treatment with the reagent followed by oxidation of the P(III) product to P(V) with, e.g. iodine: Synth. Commun., 12, 821 (1982); Synthesis, 572 (1986). The chlorophosphite has the advantage of greater reactivity over one-step phosphorylation reagents, e.g. Diphenyl phosphorochloridate, A13546.
Reagent for peptide coupling: J. Am. Chem. Soc., 74, 5304, 5309 (1952); see Appendix 6. Also useful, in the presence of TMS-OTf, in glycosidic couplings: Tetrahedron Lett., 33, 6123 (1992).
In the presence of N-ethyldiisopropylamine, reduces both aryl and alkyl nitro compounds to amines: J. Org. Chem., 63, 393 (1998). The reagent also effects dehydration of aldoximes to nitriles, deoxygenation of N-oxides and sulfoxides, and conversion of epoxides to chlorohydrins can also be effected: J. Org. Chem., 67, 711 (2002).
Hazard Statements: H226-H314-H318
Flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.