248932

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

≥98%

• Synonym(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
• Empirical Formula (Hill Notation): C₂₀H₁₃O₄P
• CAS Number: 39648-67-4
• Molecular Weight: 348.29
• Beilstein/REAXYS Number: 4713363
• MDL number: MFCD00010045
• UNSPSC Code: 12352005
• PubChem Substance ID: 24854961
• NACRES: NA.22

Properties

• assay: ≥98%
• form: solid
• optical activity: [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)
• InChI key: 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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315
• pcodes: P264 - P280 - P302 + P352 - P332 + P313 - P362 + P364
• Hazard Classifications: Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves