Skip to Content
Merck
All Photos(2)

Documents

418633

Sigma-Aldrich

Tetrabenzyl pyrophosphate

98%

Synonym(s):

Pyrophosphoric acid tetrabenzyl ester, Tetrabenzyl diphosphate

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
(C6H5CH2O)2P(O)OP(O)(OCH2C6H5)2
CAS Number:
990-91-0
Molecular Weight:
538.47
Beilstein:
2068292
MDL number:
MFCD00051941
UNSPSC Code:
12352100
PubChem Substance ID:
24866232
NACRES:
NA.22

Assay

98%

mp

63-66 °C (lit.)

storage temp.

−20°C

SMILES string

O=P(OCc1ccccc1)(OCc2ccccc2)OP(=O)(OCc3ccccc3)OCc4ccccc4

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

InChI key

NSBNXCZCLRBQTA-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Tetrabenzyl pyrophosphate may be employed for the following studies:
  • Fabrication of Pb2+-selective membrane electrodes.
  • Preparation of synthetic nucleotides, phosphates of the 3,6-dideoxyhexoses.
  • As phosphorylating reagent for the synthesis of Und-PP-Bac (undecaprenyl pyrophosphate = Und-PP; Bac = unusual sugar bacillosamine).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Solvolysis of Tetrabenzyl Pyrophosphate. Catalysis by Imidazole1
Blakeley R, et al.
Journal of the American Chemical Society, 88(1), 112-119 (1966)
Journal of the Chemical Society. Perkin Transactions 1, 729-729 (1992)
D Xu et al.
Talanta, 51(2), 365-371 (2008-10-31)
Tetrabenzyl pyrophosphate and diphenylphosphinic anhydride, with two phosphoryl groups (PO) as ligating sites, can be used as novel ionophores to make Pb(2+)-selective membrane electrodes. A good result was obtained with tetrabenzyl pyrophosphate, and the electrode based on this ionophore and
N S Utkina et al.
Bioorganicheskaia khimiia, 15(10), 1375-1383 (1989-10-01)
Interaction of lithium alcoholates of 2,4-di-O-benzoates of paratose and abequose with tetrabenzyl pyrophosphate gave alpha-phosphates of the 3,6-dideoxyhexoses, further converted into the corresponding cytidine-5'-diphosphate derivatives. These synthetic nucleotides were shown to participate in the biosynthesis of the O-specific polysaccharides for
Eranthie Weerapana et al.
Journal of the American Chemical Society, 127(40), 13766-13767 (2005-10-06)
The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service