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156311-83-0

156311-83-0 Structure

156311-83-0 Structure
IdentificationMore
[Name]

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

156311-83-0
[Synonyms]

(7-AZABENZOTRIAZOL-1-YLOXY)TRIPYRROLIDINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE
7-AZABENZOTRIAZOL-1-YLOXY-TRIS-(PYRROLIDINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE
(7-AZABENZOTRIAZOLE-1-YLOXY)TRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE
PYAOP
(7-AZABENZOTRIAZOLE-1-YLOXY)TRIPYRROLIDI
(7-Azabenzotriazol-1-yloxy)tripyrrolidinophospho
PY (7-AZABENZOTRIAZOL-1-YLOXY)TRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE
(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate
PVP-VACOPOLYMERSERIES
PYAOP ((7-AZABENZOTRIAZOL-1-YLOXY)TRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE)
3H-1,2,3-triazolo[4,5-b]pyridine phosphonium derivative
[EINECS(EC#)]

627-192-4
[Molecular Formula]

C17H27F6N7OP2
[MDL Number]

MFCD03703417
[Molecular Weight]

521.38
[MOL File]

156311-83-0.mol
Questions And AnswerBack Directory
[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 PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[HS Code ]

29339900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[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]

(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.
[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).
[reaction suitability]

reaction type: Coupling Reactions
Spectrum DetailBack Directory
[Spectrum Detail]

(3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridinato-O)tri-1-pyrrolidinylphosphonium hexafluorophosphate(156311-83-0)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

156311-83-0(sigmaaldrich)
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