| Identification | More | [Name]
Dibenzyl phosphate | [CAS]
1623-08-1 | [Synonyms]
DIBENZYL PHOSPHATE
PHOSPHORIC ACID DIBENZYL ESTER
dibenzyl hydrogen phosphate
DIBENZYL PHOSPHATE FREE ACID*CRYSTALLINE
DIBENZYLOXYPHOSPHOCREATININE
bis(phenylmethyl) ester Phosphoric acid
Bis(phenylmethyl) hydrogen phosphate
Dibenzylphosphoric acid
Phosphoric acid, bis(phenylmethyl) ester
Phosphoric acid dibenzyl
Phosphoric acid hydrogen dibenzyl ester | [EINECS(EC#)]
216-602-3 | [Molecular Formula]
C14H15O4P | [MDL Number]
MFCD00004775 | [Molecular Weight]
278.24 | [MOL File]
1623-08-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellow powder | [Melting point ]
78-80 °C (lit.) | [Boiling point ]
427.6±48.0 °C(Predicted) | [density ]
1.280±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly) | [form ]
Powder | [pka]
1.53±0.50(Predicted) | [color ]
White to slightly yellow | [BRN ]
2055755 | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C14H15O4P/c15-19(16,17-11-13-7-3-1-4-8-13)18-12-14-9-5-2-6-10-14/h1-10H,11-12H2,(H,15,16) | [InChIKey]
HDFFVHSMHLDSLO-UHFFFAOYSA-N | [SMILES]
P(O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)=O | [CAS DataBase Reference]
1623-08-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
white to slightly yellow powder | [Uses]
Eye irritant. | [Application]
Dibenzyl phosphate and its derivatives are phosphorylation reagents; for example, di-p-tolyl phosphate is one of the key intermediates in the synthesis of fosapitant dimethylglucamine. | [Definition]
ChEBI: Dibenzyl phosphate is a dialkyl phosphate. | [Synthesis]
(1) benzyl alcohol, phosphorus trichloride, triethylamine in toluene reacted to form dibenzyl phosphite (purity 69%); (2) dibenzyl phosphite, aqueous sodium hydroxide in carbon tetrachloride reacted to form dibenzyl phosphate sodium salt tetrahyd | [Precautions]
dibenzyl phosphate may be stored at 2–8 °C. It is incompatible with strong oxidizing agents. Avoid contact with skin and eyes. | [References]
[1] Bowers, S. G., Mahmud, T., & Floss, H. G. (2002). Biosynthetic studies on the α-glucosidase inhibitor acarbose: the chemical synthesis of dTDP-4-amino-4,6-dideoxy-α-d-glucose. Carbohydrate Research, 337 4, Pages 297-304. https://doi.org/10.1016/S0008-6215(01)00323-8
[2] Zhang, S.-Y., Li, Q., He, G., Nack, W. A., & Chen*, G. (2014). Pd-Catalyzed Monoselective ortho-C–H Alkylation of N-Quinolyl Benzamides: Evidence for Stereoretentive Coupling of Secondary Alkyl Iodides. Journal of the American Chemical Society, 137 1, 531–539. https://doi.org/10.1021/ja511557h
[3] Meyer, O., Ponaire, S., Rohmer, M., & Grosdemange-Billiard, C. (2006). Lewis Acid Mediated Regioselective Ring Opening of Benzylglycidol with Dibenzyl Phosphate: Short and Attractive Synthesis of Dihydroxyacetone Phosphate. Organic Letters, 8 19, 4347–4350. https://doi.org/10.1021/ol061748a
[4] Veeneman, G. H., Broxterman, H. J. G., der Marel, G. A. van, & Boom, J. H. van. (1991). An approach towards the synthesis of 1,2-trans glycosyl phosphates via iodonium ion assisted activation of thioglycosides. Tetrahedron Letters, 32 43, Pages 6175-6178. https://doi.org/10.1016/0040-4039(91)80782-2 |
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