[A13546] CAS 2524-64-3 | Diphenyl phosphorochloridate, 97%

CAS : 2524-64-3
UN# : UN3265
MDL : MFCD00003030
Hazard Class : 8
EINECS : 219-759-6
Packing Group : II

Other name :

Diphenyl chlorophosphateDiphenyl phosphoryl chloride

Chemical Properties

Formula : C12H10ClO3P
Formula weight : 268.64
Boiling Point : 145-147°/1mm
Flash point : 113°(235°F)
Density : 1.296
Refractive Index : 1.5500
Sensitivity : Moisture Sensitive. Ambient temperatures.
Form : Liquid
Solubility : Immiscible with water.

Literature 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.

Notes

Moisture sensitive. Incompatible with strong bases and strong oxidizing agents.Other References:Beilstein: 654130UN#: UN3265

Grade Specifications

Grade Specifications

Hazard Statements : H314-H318Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501aDo not breathe dust/fume/gas/mist/vapours/spray.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.IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.