693022

(S)-DM-BINAP

• Synonym(s): (S)-(−)-2,2′-Bis[bis(3,5-dimethylphenyl)phosphino]-1,1′-binaphthyl, (S)-(−)-2,2′-Bis[di(3,5-xylyl)phoshino]-1,1′-binaphthyl, (S)-3,5-Xylyl-BINAP
• Empirical Formula (Hill Notation): C₅₂H₄₈P₂
• CAS Number: 135139-00-3
• Molecular Weight: 734.89
• MDL number: MFCD01630821
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761554

Properties

• form: solid
• optical activity: [α]/D -172°, 20, c = 1 in chloroform
• mp: 189-193 °C
• SMILES string: Cc1cc(C)cc(c1)P(c2cc(C)cc(C)c2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7cc(C)cc(C)c7)c8cc(C)cc(C)c8
• InChI: 1S/C52H48P2/c1-33-21-34(2)26-43(25-33)53(44-27-35(3)22-36(4)28-44)49-19-17-41-13-9-11-15-47(41)51(49)52-48-16-12-10-14-42(48)18-20-50(52)54(45-29-37(5)23-38(6)30-45)46-31-39(7)24-40(8)32-46/h9-32H,1-8H3
• InChI key: MXGXXBYVDMVJAO-UHFFFAOYSA-N

Description

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Catalyst for:

• Asymmetric hydrogenation of benzophenone
• Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives in the presence of chiral biaryl bisphosphine ligands
• Regiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolates
• Ligand controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids to form regioisomeric arylcyclopentenols
• Platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature
• Stereoselective preparation of chiral N,O-biaryls via Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes

Legal Information

Sold in collaboration with Takasago for research purposes only.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves