Diethyl chlorophosphite, 97%, Thermo Scientific Chemicals

General References:

1. 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.
2. 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.
3. 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.
4. 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).
5. 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).