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Tetrabenzyl pyrophosphate

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Tetrabenzyl pyrophosphate Basic information

Product Name:
Tetrabenzyl pyrophosphate
Synonyms:
  • PYROPHOSPHORIC ACID TETRABENZYL ESTER
  • TETRABENZYL PYROPHOSPHATE
  • TETRABENZYL DIPHOSPHATE
  • Tetrabenzyl pyrophosphate, tech.
  • Pyrophosphoric acid tetrabenzyl ester, Tetrabenzyl diphosphate
  • Bis(phenylmethoxy)phosphoryl bis(phenylmethyl) phosphate
  • Benzyl Pyrophosphate
  • Diphosphoric Acid P,P,P',P'-Tetrakis(phenylMethyl) Ester
CAS:
990-91-0
MF:
C28H28O7P2
MW:
538.47
EINECS:
628-817-3
Product Categories:
  • Phosphorylating and Phosphitylating Agents
  • Biochemistry
  • Nucleosides, Nucleotides & Related Reagents
  • Phosphorylating and Phosphorothioating Agents
  • Phosphorylation
  • Protecting Agents, Phosphorylating Agents & Condensing Agents
  • Synthetic Organic Chemistry
Mol File:
990-91-0.mol
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Tetrabenzyl pyrophosphate Chemical Properties

Melting point:
63-66 °C (lit.)
Boiling point:
601.6±55.0 °C(Predicted)
Density 
1.289±0.06 g/cm3(Predicted)
vapor pressure 
0.001Pa at 140℃
storage temp. 
-20°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Powder or Crystalline Powder
color 
White to off-white
Water Solubility 
Slightly soluble in water.
Sensitive 
Moisture Sensitive
BRN 
2068292
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
SMILES
P(=O)(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)OP(=O)(OCC1C=CC=CC=1)OCC1C=CC=CC=1
CAS DataBase Reference
990-91-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-36/37/39-45
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
10-21
HazardClass 
8
PackingGroup 
II
HS Code 
29209090

MSDS

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Tetrabenzyl pyrophosphate Usage And Synthesis

Chemical Properties

White Solid

Uses

Tetrabenzyl pyrophosphate is used in the preparation of phosphoryl derivatives of shikimic acid in the presence of LDA. It is used in the preparation of dibenzyl phosphoro fluoridate in the presence of cesium fluoride as a catalyst. It is also used as a precursor in pharmaceuticals and involved in the phosphorylation of inositol derivatives.

Uses

Phosphorylating reagent.

Preparation

The production of tetrabenzyl pyrophosphate by the action of acyl chlorides on dibenzyl hydrogen phosphate, and a novel reaction of tetraphenyl pyrophosphate.
Preparation of Tetrabenzyl Pyrophosphate: A flask fitted with a nitrogen inlet, overhead stirrer, teflon-coated thermocouple probe, and pressure-equalizing addition funnel was charged with 350 milliliters of dry (water content ≦50 μg/mL), peroxide-free tetrahydrofuran, followed by 50.0 grams (174 millimoles) of dibenzylphosphoric acid (DBP), and the resulting mixture was stirred until the solid dissolved (about 10-15 minutes). A solution of 18.9 grams (91.6 millimoles) of dicyclohexylcarbodiimide (DCC) in 215 milliliters of THF was added from the addition funnel to a stirred, cooled (water-bath) solution of DBP at a rate to maintain the temperature at about 20°-25° C. The reaction is slightly exothermic and the addition took about 30 minutes. Within minutes, a precipitate of dicyclohexylurea formed in the mixture. Stirring was continued for about 2 hours at 20°-25° C. The reaction was monitored by HPLC assay using VYDAC C-18 (300A, 4.6×250 mm) column with water (0.02M KH2PO4) acetonitrile as eluent. The reaction was complete in about 1 hour (assay showing <2 percent unreacted DBP). The mixture was then filtered while excluding moisture to remove dicyclohexylurea. The filter cake was washed with two 25 milliliter portions of THF. The solution when assayed by HPLC showed 45.9 grams (98 percent) yield of tetrabenzyl pyrophosphate (TBPP) in 620 milliliters of THF (0.137M). The filtrate was then stored at 0° C. with exclusion of moisture until the next step.

Tetrabenzyl pyrophosphate Preparation Products And Raw materials

Raw materials

Tetrabenzyl pyrophosphateSupplier

Bengbu Nako Chemical Co., Ltd. Gold
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0552-3068102 13966060073
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sales@nakochem.com
Hefei TianRui Pharmaceutical Chemistry Co., Ltd. Gold
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0551-68933033 13956024211
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trchem@163.com
Chongqing Xingcan Pharmaceutical Technology Co., Ltd. Gold
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15523000485
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xingcanyaoye@sina.com
J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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4006608290; 18621169109
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market03@meryer.com