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18565

Sigma-Aldrich

Bromotripyrrolidinophosphonium hexafluorophosphate

≥95.0% (HPLC), for peptide synthesis

Synonym(s):

PyBroP®

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About This Item

Empirical Formula (Hill Notation):
C12H24BrF6N3P2
CAS Number:
132705-51-2
Molecular Weight:
466.18
Beilstein/REAXYS Number:
6842340
MDL number:
MFCD00077412
UNSPSC Code:
12352107
PubChem Substance ID:
57647747
NACRES:
NA.22

product name

Bromotripyrrolidinophosphonium hexafluorophosphate, ≥95.0% (HPLC)

Quality Level

100

assay

≥95.0% (HPLC)

form

solid

reaction suitability

reaction type: Coupling Reactions

application(s)

peptide synthesis

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

Related Categories

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.

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
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ0959
BCCJ0958
BCCC0215
BCBW3388
BCBQ4202V

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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)
Nickel-Catalyzed Cross-Coupling of Phenols and Arylboronic Acids Through an In Situ Phenol Activation Mediated by PyBroP.
Chen GJ, et al.
Chemistry?A European Journal , 17(14), 4038-4042 (2011)
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