248932

(R)-(−)-1,1′-Binaphthyl-2,2′-diylhydrogenphosphat

≥98%

• Synonym(e): (R)-(−)-1,1′-Binaphthalin-2,2′-diyl-hydrogen-phosphat, (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxid
• Empirische Formel (Hill-System): C₂₀H₁₃O₄P
• CAS-Nummer: 39648-67-4
• Molekulargewicht: 348.29
• Beilstein: 4713363
• MDL-Nummer: MFCD00010045
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24854961
• NACRES: NA.22

Eigenschaften

• Assay: ≥98%
• Form: solid
• Optische Aktivität: [α]20/D −605°, c = 1.35 in methanol
• InChI: 1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)
• InChIKey: JEHUZVBIUCAMRZ-UHFFFAOYSA-N

Beschreibung

Anwendung

A chiral ligand used in hydrocarboxylation reactions. Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds. A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid. Palladium derivatives have been used in asymmetric hydrocarboxylations, and rhodium derivatives have been used in dipolar cycloadditions.

Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate is an organocatalyst that can be used:       

• To facilitates the controlled ring-opening homopolymerization and copolymerization of ε-caprolactone (cyclic ester).        
• As an additive along with a copper catalyst to achieve the highest catalytic activity in Sonogashira-type reactions.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315
• P-Sätze: P264 - P280 - P302 + P352 - P332 + P313 - P362 + P364
• Gefahreneinstufungen: Skin Irrit. 2
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves