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2524-64-3 - Diphenyl phosphorochloridate, 97% - Diphenyl chlorophosphate - Diphenyl phosphoryl chloride - A13546 - Alfa Aesar

A13546 Diphenyl phosphorochloridate, 97%

Codice CAS
Diphenyl chlorophosphate
Diphenyl phosphoryl chloride

Dimensioni Prezzo ($) Quantità Disponibilità
50g 25,00
250g 67,40
1000g 220,00
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Diphenyl phosphorochloridate, 97%


Proprietà chimiche

Peso formula
Punto di ebollizione
Punto di infiammabilità
Indice di rifrazione
Moisture Sensitive
Immiscible with water.


Diphenyl phosphorochloridate is used to prepare cyclohexyl-amidophosphoric acid diphenyl ester by reacting with cyclohexylamine. It is also used in the synthesis of alfa-substituted beta-lactams, anhydrides, esters and thioesters. It is also employed in the conversion of aldoximes to nitriles. Further, it is used in the preparation and reaction of enol phosphates, guanosine-adenosine-5',5'-triphosphate, guanosine-cytidine-5',5'-triphosphate, guanosine-uridine-5',5'-triphosphate, diguanosine-5',5'-diphosphate and diguanosine-5',5'-triphosphate. In addition to this, it serves as a phosphorylating agent for the preparation of 2-deoxy-D-galactose-3 and -6 phosphoric acids.


Moisture sensitive. Incompatible with strong bases and strong oxidizing agents.


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.

Xu, Z. A review on the chemical synthesis of pyrophosphate bonds in bioactive nucleoside diphosphate analogs. Bioorg. Med. Chem. Lett. 2015, 25 (18), 3777-3783.

Marquick, A. L.; Montero, J. L.; Lebrun, A.; Barragan-Montero, V. Straightforward synthesis towards mono and bis-phosphonic acid functionalised beta-cyclodextrins. Tetrahedron 2015, 71 (10), 1616-1621.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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.

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