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Tributylammonium pyrophosphate

Tributylammonium pyrophosphate Structure
CAS No.
5975-18-8
Chemical Name:
Tributylammonium pyrophosphate
Synonyms
Bis(tributylaMMoniuM) Pyrophosphate;tributylamine diphosphate;TRIBUTYLAMMONIUM PYROPHOSPHATE;PYROPHOSPHATE, TRIBUTYLAMMONIUM;Tributyl Ammonium Pyrophosphate (TBAP);Tri-n-butylammonium pyrophosphate, 95%;Bis(tri-n-butylammonium) pyrophosphate;Tributylammonium pyrophosphate (50% wt in ACN);Diphosphoric Acid compd. with N,N-Dibutyl-1-butanamine (1:2)
CBNumber:
CB8743916
Molecular Formula:
C12H31NO7P2
Molecular Weight:
363.33
MOL File:
5975-18-8.mol
Modify Date:
2024/5/20 11:55:08

Tributylammonium pyrophosphate Properties

Melting point 78 - 83°C
storage temp. -20°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form Solid
color White to Off-White
Stability Hygroscopic
InChI InChI=1S/C12H27N.H4O7P2/c1-4-7-10-13(11-8-5-2)12-9-6-3;1-8(2,3)7-9(4,5)6/h4-12H2,1-3H3;(H2,1,2,3)(H2,4,5,6)
InChIKey WJFREWBMJPXLBS-UHFFFAOYSA-N
SMILES N(CCCC)(CCCC)CCCC.O(P(O)(O)=O)P(O)(O)=O

SAFETY

Risk and Safety Statements

WGK Germany  3

Tributylammonium pyrophosphate price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) P8533 Tributylammonium pyrophosphate 5975-18-8 250MG ₹4265.05 2022-06-14 Buy
Sigma-Aldrich(India) P8533 Tributylammonium pyrophosphate 5975-18-8 1G ₹13033.3 2022-06-14 Buy
Sigma-Aldrich(India) P8533 Tributylammonium pyrophosphate 5975-18-8 5G ₹53930.15 2022-06-14 Buy
Product number Packaging Price Buy
P8533 250MG ₹4265.05 Buy
P8533 1G ₹13033.3 Buy
P8533 5G ₹53930.15 Buy

Tributylammonium pyrophosphate Chemical Properties,Uses,Production

Description

Tributylammonium pyrophosphate is a phosphorylating reagent used in the synthesis of phosphorylated nucleosides, particularly nucleoside triphosphates used as building blocks for the synthesis of DNA, RNA and sugar nucleotides; as well as a source of cellular energy. Nucleoside triphosphates are typically synthesised by treating free nucleosides with phosphorus oxychloride, then adding tributylammonium pyrophosphate to the reaction intermediate, where the lipophilic tributylammonium salt enhances solubility in organic solvents. Additionally, tributylammonium pyrophosphate was used in the preparation of structurally complex dinucleotide-5’-triphosphates.

Uses

Bis(tributylammonium) Pyrophosphate is an phosphorylating reagent used in the synthesis of phosphorylated deoxynucleosides.
Reactant for:
Enzymic synthesis of 3′-deoxy-apio-nucleic acid duplexes
Synthesis of deoxynucleoside S-methylphosphonic acids
Preparation of fluorescent non-nucleotide ATP analog N-methylanthraniloylamideethyl triphosphate
Useful in triphosphate synthesis because of its low water content and high solubility in organic solvents.

Preparation

A solution of tetrasodium pyrophosphate (3.5 g, 7.5 mmol) in water (50 mL) was eluted through a cation exchange resin (BIO-RAD AG 50 W-X8 Resin, 50–100 mesh, hydrogen form) at 4 °C. The eluent with pH of less than 3 (pH paper) was collected directly into a vigorously stirred flask containing tributylamine (2 mL, 8 mmol, 4 °C). The obtained tributylammonium pyrophosphate was dried through repeated rotary evaporation with dry MeOH and then dissolved in dry DMF (10 mL).

General Description

Tributylammonium pyrophosphate is a phosphorylating reagent used in the synthesis of modified dNTPs (deoxynucleoside triphosphates) which are important building blocks for the generation of DNA, RNA, functionalized nucleic acids.

References

Santner et al (2012). The synthesis of 2′-methylseleno adenosine and guanosine 5′-triphosphates. Bioorganic and Medicinal Chemistry 20:2416.
Hollenstein (2012). Nucleoside Triphosphates — Building Blocks for the Modification of Nucleic Acids. Molecules 17:13569-13591.
bramova et al (2007). A facile and effective synthesis of dinucleotide 5′-triphosphates. Bioorganic and Medicinal Chemistry 15:6549-6555.

Tributylammonium pyrophosphate Preparation Products And Raw materials

Raw materials

Preparation Products

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TRIBUTYLAMMONIUM PYROPHOSPHATE PYROPHOSPHATE, TRIBUTYLAMMONIUM Tri-n-butylammonium pyrophosphate, 95% Diphosphoric Acid compd. with N,N-Dibutyl-1-butanamine (1:2) Bis(tributylaMMoniuM) Pyrophosphate Tributyl Ammonium Pyrophosphate (TBAP) Tributylammonium pyrophosphate (50% wt in ACN) Bis(tri-n-butylammonium) pyrophosphate tributylamine diphosphate 5975-18-8 Phase Transfer Catalysts Synthetic Reagents Ammonium Salts 1