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

A13546 Diphenyl phosphorochloridate, 97%

Numéro de CAS
2524-64-3
Synonymes
Diphenyl chlorophosphate
Diphenyl phosphoryl chloride

Conditionnement Prix ($) Quantité Disponibilité
50g 25,00
250g 67,40
1000g 220,00
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Diphenyl phosphorochloridate, 97%

MDL
MFCD00003030
EINECS
219-759-6

Propriétés chimiques

Formule
C12H10ClO3P
Poids moleculaire
268.64
Point d'ébullition
145-147°/1mm
Point d'éclair
113°(235°F)
Densité
1.296
Indice de réfraction
1.5500
Sensibilité
Moisture Sensitive
Solubilité
Immiscible with water.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

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

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

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.

Autres références

Beilstein
654130
Classe de danger
8
Groupe d'emballage
III
Code tarifaire harmonisé
2920.90
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire