248932

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

≥98%

• Synonyme(s) : (R)-(−)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate, (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide
• Formule empirique (notation de Hill): C₂₀H₁₃O₄P
• Numéro CAS: 39648-67-4
• Poids moléculaire : 348.29
• Numéro Beilstein : 4713363
• Numéro MDL: MFCD00010045
• Code UNSPSC : 12352005
• ID de substance PubChem : 24854961
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: ≥98%
• Forme: solid
• Activité optique: [α]20/D −605°, c = 1.35 in methanol
• Groupe fonctionnel: phosphate
• 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)
• Clé InChI: JEHUZVBIUCAMRZ-UHFFFAOYSA-N

Description

Application

(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.

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.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315
• Conseils de prudence: P264 - P280 - P302 + P352 - P332 + P313 - P362 + P364
• Classification des risques: Skin Irrit. 2
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves