dibenzyl {[bis(benzyloxy)phosphoryl]oxy}phosphonate

• ChemBase ID: 145026
• Molecular Formular: C28H28O7P2
• Molecular Mass: 538.465242
• Monoisotopic Mass: 538.1310265
• SMILES: c1ccc(cc1)COP(=O)(OCc1ccccc1)OP(=O)(OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: O=P(OP(=O)(OCc1ccccc1)OCc1ccccc1)(OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C28H28O7P2/c29-36(31-21-25-13-5-1-6-14-25,32-22-26-15-7-2-8-16-26)35-37(30,33-23-27-17-9-3-10-18-27)34-24-28-19-11-4-12-20-28/h1-20H,21-24H2
• InChIKey: NSBNXCZCLRBQTA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dibenzyl {[bis(benzyloxy)phosphoryl]oxy}phosphonate
• IUPAC Traditional name: dibenzyl (dibenzyloxyphosphoryl)oxyphosphonate
• Synonyms: Pyrophosphoric acid tetrabenzyl ester; Tetrabenzyl diphosphate; Tetrabenzyl pyrophosphate; Tetrabenzyl diphosphate; Diphosphoric Acid P,P,P',P'-Tetrakis(phenylmethyl) Ester; Benzyl Pyrophosphate; Tetrabenzyl Pyrophosphate; 四苄基二磷酸酯; 焦磷酸四苄基酯; 焦磷酸四苄酯

Database IDs

• CAS Number: 990-91-0
• MDL Number: MFCD00051941
• Beilstein Number: 2068292
• PubChem SID: 162239236; 24888765; 24866232
• PubChem CID: 563183

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.967833
• LogD (pH = 7.4): 6.967833
• Log P: 6.967833
• Molar Refractivity: 141.9044 cm^3
• Polarizability: 56.48918 Å^3
• Polar Surface Area: 80.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 58-60°C; 58-64°C; 61-64 °C; 63-66 °C(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (HPLC); 97%; 98%
• Grade: puriss.
• Linear Formula: (C6H5CH2O)2P(O)OP(O)(OCH2C6H5)2

DETAILS

Sigma Aldrich - 418633

Packaging
1 g in glass bottle
Application
Phosphorylating agent1 which has been employed in inositol phosphorylation.2

Sigma Aldrich - 86740

Other Notes
Reagent used for the smooth phosphorylation of sensitive alcohols, especially polyols1,2,3,4

Toronto Research Chemicals - T289450

Phosphorylating reagent.

REFERENCES

• Moris, M., et al.: J. Med. Chem., 48, 1251 (2005)
• Kline, T., et al.: Bioorg. Med. Chem. Lett., 18, 1507 (2005)
• Useful reagent for O-phosphorylation. Used in preparation of phosphoryl derivatives of shikimic acid, by reaction in the presence of LDA; subsequent debenzylation was accomplished with TMS bromide: J. Org. Chem, 51, 75 (1986). Used to phosphorylate inositol derivatives in the presence of KH or NaH in THF: J. Am. Chem. Soc., 109, 3478 (1987); J. Chem. Soc., Chem. Commun., 298 (1991); the required debenzylated products were obtained by catalytic hydrogenolysis.