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12805 Sigma-Aldrich

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

purum, ≥97.0% (TLC)

Synonym: PyBOP®

  • CAS Number 128625-52-5

  • Linear Formula C18H28N6OP · PF6

  • Molecular Weight 520.39

  •  Beilstein/REAXYS Number 3584612

  •  MDL number MFCD00077411

  •  PubChem Substance ID 329749882

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Peptide Coupling, Peptide Synthesis and Peptide Chemistry, Phosphonium/Uronium/Formamidinium More...
grade   purum
assay   ≥97.0% (TLC)
mp   ~150 °C
  154-156 °C (dec.) (lit.)
storage temp.   2-8°C
SMILES string   F[P-](F)(F)(F)(F)F.C1CCN(C1)[P+](On2nnc3ccccc23)(N4CCCC4)N5CCCC5
InChI   1S/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1
InChI key   VIAFLMPQBHAMLI-UHFFFAOYSA-N

Description

General description

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) is an activator of carboxyl group commonly used in peptide synthesis. It also participates in the carboxylic acid esterification. It shows characteristics similar to benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and can be utilized as an alternative to BOP in peptide bond formation.

Application

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) may be used in the following studies:
• As coupling reagent in the preparation strategies for peptide-oligonucleotide conjugates.
• Synthesis of structured pure triacylglycerol (TAG) regioisomers.
• As coupling reagent in the synthesis of a 3,5-pyrazolidinedione on soluble polyethylene glycol (PEG) polymer support.
• Synthesis of herceptin- nanoparticles.

Analogue of the BOP coupling reagent which does not form carcinogenic HMPA as by-product.

Legal Information

PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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