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
• NACRES: NA.22
• PubChem Substance ID: 57647747
• UNSPSC Code: 12352107
• MDL number: MFCD00077412
• Beilstein/REAXYS Number: 6842340

Eigenschaften

• Produktname: Brom-tripyrrolidinophosphonium-hexafluorophosphat, ≥95.0% (HPLC)
• Quality Segment: 100
• 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

Beschreibung

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

Sicherheitshinweise

• signalword: Danger
• Lagerklasse: 8A - Combustible corrosive hazardous materials
• wgk: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves
• pictograms: GHS05,GHS07
• hcodes: H302,H314
• pcodes: P260 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
• flash_point_f: No data available
• flash_point_c: No data available