18565
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:
Molecular Weight:
466.18
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352107
MDL number:
Beilstein/REAXYS Number:
6842340
Product Name
Bromotripyrrolidinophosphonium hexafluorophosphate, ≥95.0% (HPLC)
Quality Segment
assay
≥95.0% (HPLC)
form
solid
reaction suitability
core: phosphonium, 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
Application
Catalyst for:
Synthesis of primary amides
Direct dehydrative phosphonium cross coupling
Direct arylation
Pyrrolidide formation by phosphonium salt coupling reagents
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:
It can also be used as an activating 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
signalword
Danger
hcodes
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
flash_point_f
No data available
flash_point_c
No data available
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