18565

Brom-tripyrrolidinophosphonium-hexafluorophosphat

≥95.0% (HPLC), for peptide synthesis

• Synonym(e): PyBroP^®
• Empirische Formel (Hill-System): C₁₂H₂₄BrF₆N₃P₂
• CAS-Nummer: 132705-51-2
• Molekulargewicht: 466.18
• Beilstein: 6842340
• MDL-Nummer: MFCD00077412
• UNSPSC-Code: 12352107
• PubChem Substanz-ID: 57647747
• NACRES: NA.22

Eigenschaften

• product name: Brom-tripyrrolidinophosphonium-hexafluorophosphat, ≥95.0% (HPLC)
• Assay: ≥95.0% (HPLC)
• Form: solid
• Eignung der Reaktion: reaction type: Coupling Reactions
• Anwendung(en): peptide synthesis
• Lagertemp.: −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
• InChIKey: CYKRMWNZYOIJCH-UHFFFAOYSA-N

Beschreibung

Anwendung

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.

Sonstige Hinweise

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

Rechtliche Hinweise

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

Sicherheitshinweise

• Piktogramme: GHS05
• Signalwort: Danger
• H-Sätze: H314
• P-Sätze: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Gefahreneinstufungen: Eye Dam. 1 - Skin Corr. 1B
• Lagerklassenschlüssel: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves