Diphenyl phosphorochloridate

• Catalog No.: A13546
• CAS Number: 2524-64-3
• M. F.: C12H10ClO3P
• M. W.: 268.632761
• Purity: 97%

SYNONYMS

• Title: 氯磷酸二苯酯
• IUPAC name: diphenyl chlorophosphonate
• IUPAC Traditional name: diphenyl chlorophosphonate
• Synonyms: Diphenyl chlorophosphate; Diphenyl phosphoryl chloride

DATABASE IDS

• EC Number: 219-759-6
• Beilstein Number: 654130
• CAS Number: 2524-64-3
• MDL Number: MFCD00003030

PROPERTIES

• Purity: 97%
• Boiling Point: 145-147°C/1mm
• Density: 1.296
• Flash Point: 113°C(235°F)
• Refractive Index: 1.5500
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3265
• Packing Group: III

REFERENCES

• Diphenylphosphate esters, formed with or without catalysis by DMAP, undergo a variety of transformations:
• Hydrogenolysis of the phenyl groups yields the monophosphate ester of the alcohol. Glycosyl monophosphates have been prepared in this way. Alternatively, treatment of the glycosyl diphenyl phosphate with sodium azide in DMF provides a high yield route to glycosyl azides: Carbohydr. Res., 223, 169 (1992).
• Diphenylphosphate has also been exploited as a good leaving group in the high yield conversion (equivalent to dehydration) of secondary alcohols to olefins by thermal elimination: Synthesis, 1300 (1995). For further information, see Triphenyl phosphate, L08130. Other conversions, generally in the presence of a base such as triethylamine, in which the equivalent of a dehydration step occurs are:
• Aldoximes to nitriles at room temperature: J. Org. Chem., 34, 2805 (1969). Peptide coupling (see Appendix 6), via the mixed carboxyl phosphate anhydride: Chem. Ber., 94, 2644 (1961). Carboxylic acids to anhydrides: Synthesis, 219 (1981). ω-Hydroxy acids to macrolides, promoted by DMAP: J. Org. Chem., 47, 1612 (1982).
• Lithium enolates give enol diphenylphosphates in which the phosphate moiety acts as a leaving group; e.g., ketone enol phosphates have been converted to the corresponding alkene by reaction with organocuprates: Tetrahedron Lett., 4405 (1976). With amides, internal displacement occurs; subsequent reaction with NaN₃ gives azirines: Helv. Chim. Acta, 76, 2830 (1993):
  
• See also Diphenylphosphonic azide, A12124.