ChemicalBook Product Catalog Biochemical Engineering Condensing agent (3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate

(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate

Product Name(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate
CAS156311-83-0
MFC17H27F6N7OP2
MW521.39
EINECS627-192-4
MOL File156311-83-0.mol

Chemical Properties

Melting point	163-168 °C(lit.)
RTECS	TH3890000
storage temp.	-20°C
solubility	Soluble in water or 1% acetic acid
form	Powder or Crystalline Powder
color	White to off-white
Water Solubility	Soluble in water.
Major Application	peptide synthesis
InChI	InChI=1S/C17H27N7OP.F6P/c1-2-11-21(10-1)26(22-12-3-4-13-22,23-14-5-6-15-23)25-24-17-16(19-20-24)8-7-9-18-17;1-7(2,3,4,5)6/h7-9H,1-6,10-15H2;/q+1;-1
InChIKey	CBZAHNDHLWAZQC-UHFFFAOYSA-N
SMILES	[P+5]([F-])([F-])([F-])([F-])([F-])[F-].[P+](N1CCCC1)(N1CCCC1)(N1CCCC1)ON1N=NC2C=CC=NC1=2
CAS DataBase Reference	156311-83-0(CAS DataBase Reference)
EPA Substance Registry System	Phosphorus(1+), [3-(hydroxy-.kappa.O)-3H-1,2,3-triazolo[4,5-b]pyridinato]tri-1-pyrrolidinyl-, (T-4)-, hexafluorophosphate(1-) (1:1) (156311-83-0)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29339900
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Synthesis

In a dry 250 mL reaction flask, anhydrous triethylamine (655 μmol) was added to a solution of bromo-tris(pyrrolidine)phosphine hexafluorophosphine (2.19 g) and 1-hydroxy-7-azabenzyltriazole (4.70 mmol) in anhydrous dichloromethane (8 mL). The resulting reaction mixture was stirred at room temperature for 2 hours. After the reaction was complete, anhydrous diethyl ether was added to the reaction system, and a solid was observed to precipitate. The precipitate was collected on a filter and washed successively with water (3 x 25 mL) and anhydrous diethyl ether (2 x 25 mL). Finally, the precipitate was recrystallized from acetone/diethyl ether to obtain the target product.

Synthetic route of (3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate

Figure: Synthetic route of (3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate

Chemical Properties

(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate is white to off-white crystalline powder

Uses

PyAOP is a phosphonium salt used as a coupling reagent in solid-phase peptide synthesis, without undergoing side reactions with the amino terminus. PyAOP is a derivative of HOAt (H805070).

Uses

(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate is used as a coupling reagent in solid phase peptide synthesis. It is preferred over HATU, because it does not side react at the N-terminus of the peptide. Compared to the HOBt derivates, PyAOP (and HOAt in general) are more reactive due to the additional nitrogen.

reaction suitability

reaction type: Coupling Reactions

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