Diethyl chlorophosphite

• Catalog No.: L09919
• CAS Number: 589-57-1
• M. F.: C4H10ClO2P
• M. W.: 156.547761
• Purity: 97%

SYNONYMS

• Title: 氯代亚磷酸二乙酯
• IUPAC name: diethyl chlorophosphonite
• IUPAC Traditional name: ethyl phosphorochloridite
• Synonyms: Diethyl phosphorochloridite

DATABASE IDS

• MDL Number: MFCD00009074
• EC Number: 209-652-2
• CAS Number: 589-57-1
• Beilstein Number: 1098392
• Merck Index: 143841

PROPERTIES

• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2920
• Packing Group: II
• GHS Hazard statements: H314-H318-H226
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-14-34
• Safety Statements: 26-36/37/39-45
• Purity: 97%
• Boiling Point: 153-155°C
• Density: 1.082
• Flash Point: 25°C(77°F)
• Refractive Index: 1.4375

REFERENCES

• 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).