18565

Sigma-Aldrich

Bromotripyrrolidinophosphonium hexafluorophosphate

≥95.0% (HPLC)

Synonym(s):
PyBroP
Empirical Formula (Hill Notation):
C12H24BrF6N3P2
CAS Number:
Molecular Weight:
466.18
Beilstein/REAXYS Number:
6842340
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0% (HPLC)

reaction suitability

reaction type: Coupling Reactions

application(s)

peptide synthesis: suitable

storage temp.

−20°C

SMILES string

F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N2CCCC2)N3CCCC3

InChI

1S/C12H24BrN3P.F6P/c13-17(14-7-1-2-8-14,15-9-3-4-10-15)16-11-5-6-12-16;1-7(2,3,4,5)6/h1-12H2;/q+1;-1

InChI key

CYKRMWNZYOIJCH-UHFFFAOYSA-N

Application

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.

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

Packaging

5, 25 g in poly bottle
1 g in poly tube

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

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C-OH Bond Activation Using PyBrOP.
Shi C and Aldrich CC
Organic Letters, 12(10), 2286-2289 (2010)
Ni-catalyzed construction of C-P bonds from electron-deficient phenols via the in situ aryl C-O activation by PyBroP.
Zhao YL, et al.
Chemical Communications (Cambridge, England), 48(47), 5868-5870 (2012)
Efficient Conversion of Biginelli 3, 4-Dihydropyrimidin-2 (1 H)-one to Pyrimidines via PyBroP-Mediated Coupling.
Kang FA, et al.
The Journal of Organic Chemistry, 70(5), 1957-1960 (2005)
PyBroP: a convenient activator for the synthesis of formamidines.
Delarue S and Sergheraert C
Tetrahedron Letters, 40(30), 5487-5490 (1999)
T. Kurome et al.
Tetrahedron, 52, 4327-4327 (1996)

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