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418633

Sigma-Aldrich

Tetrabenzyl pyrophosphate

98%

Synonym(s):

Pyrophosphoric acid tetrabenzyl ester, Tetrabenzyl diphosphate

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₹9,760.00

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

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Quality Level

200

Assay

98%

mp

63-66 °C (lit.)

functional group

phenyl
phosphate

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

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1 of 4

This Item
933971659568.21197
Tetrabenzyl pyrophosphate 98%

418633

Tetrabenzyl pyrophosphate

Tris(tetrabutylammonium) hydrogen pyrophosphate ≥97.0% (calc. on dry substance, T)

93397

Tris(tetrabutylammonium) hydrogen pyrophosphate

Methyl benzenesulfonate 98%

165956

Methyl benzenesulfonate

Triphenyl phosphate for synthesis

8.21197

Triphenyl phosphate

assay

98%

assay

≥97.0% (calc. on dry substance, T)

assay

98%

assay

≥99.0% (GC)

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

mp

63-66 °C (lit.)

mp

-

mp

-

mp

48-50 °C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-30°C

functional group

phenyl

functional group

amine, phosphate

functional group

sulfonic acid

functional group

-

Application

Tetrabenzyl pyrophosphate may be employed for the following studies:
  • Fabrication of Pb2+-selective membrane electrodes.[1]
  • Preparation of synthetic nucleotides, phosphates of the 3,6-dideoxyhexoses.[2]
  • As phosphorylating reagent for the synthesis of Und-PP-Bac (undecaprenyl pyrophosphate = Und-PP; Bac = unusual sugar bacillosamine).[3]

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
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    Certificates of Analysis (COA)

    Lot/Batch Number
    BGBC3223V
    BGBC2860V
    BCBF9560V
    BCBF2933V
    BCBB1332V

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    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
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