• USA Home
  • 18565 - Bromotripyrrolidinophosphonium hexafluorophosphate

EMAIL THIS PAGE TO A FRIEND
18565 Sigma-Aldrich

Bromotripyrrolidinophosphonium hexafluorophosphate

≥95.0% (HPLC)

Synonym: PyBroP®

  • CAS Number 132705-51-2

  • Empirical Formula (Hill Notation) C12H24BrF6N3P2

  • Molecular Weight 466.18

  •  Beilstein/REAXYS Number 6842340

  •  MDL number MFCD00077412

  •  PubChem Substance ID 57647747

  •  NACRES NA.22

Purchase

Properties

Related Categories Chemical Biology, Chemical Synthesis, Coupling, Peptide Coupling, Peptide Synthesis and Peptide Chemistry,
InChI Key   CYKRMWNZYOIJCH-UHFFFAOYSA-N
assay   ≥95.0% (HPLC)
storage temp.   −20°C

Description

Application

Catalyst for:
Synthesis of primary amides
Direct dehydrative phosphonium cross coupling
Direct arylation
Pyrrolidide formation by phosphonium salt coupling reagents

It can be used as a coupling reagent:
• For Suzuki–Miyaura cross-coupling of phenols and arylboronic acids to synthesize biaryls and heterobiaryls.
• To functionalize pyrimidines (synthesized from 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) via the Kappe dehydrogenation) by using various nucleophiles.
• To synthesize formamidines by coupling with various primary amines and N,N-diisopropylethylamine.

It can also be used as an activating reagent:
• For the activation of C-OH bond in tautomerizable heterocycles to form the phosphonium salt which aids the Sonogashira coupling of heterocycles with various alkynes.
• For the one–pot activation of C-O bond in phenols and further coupling reaction with phosphine oxide or phosphite to form C-P bonds.

Packaging

1 g in poly tube

5, 25 g in poly bottle

Other Notes

Reactive peptide coupling reagent suitable for α,α-dialkyl amino acids; Synthesis of depsipeptides

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Phosphonium Salts

Phosphonium salts are powerful and easy-to-use peptide coupling reagents that allow in situ generation of active esters. After the recognition of chlorotris(dimethylamino)phosphonium as the activatin...
Matthias Junkers
ChemFiles 2007, 7.2, 8.
Keywords: Peptide synthesis

Related Content

COMU – Safer and More Efficient Peptide Coupling Reagent

Peptide synthesis relies heavily on efficient and reliable coupling reagents. A low tendency for racemization is a key requirement. This is especially true for solid phase peptide synthesis—quantitat...
Keywords: Building blocks, Calorimetry, Condensations, Coupling reactions, Epimerizations, PEGylations, Peptide synthesis, Racemizations, Solid phase peptide synthesis, Solvents

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

06693 Timestrip Plus -20 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?