693030

(S)-T-BINAP

• Synonym(s): (S)-(−)-2,2′-p-tolyl-phosphino)-1,1′-binaphthyl, (S)-Tol-BINAP
• Empirical Formula (Hill Notation): C₄₈H₄₀P₂
• CAS Number: 100165-88-6
• Molecular Weight: 678.78
• MDL number: MFCD01311709
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761556
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• optical activity: [α]20/D -156°, c = 0.5 in benzene
• mp: 250-255 °C
• functional group: phosphine
• SMILES string: P(c8ccc(cc8)C)(c7ccc(cc7)C)c1c(c6c(cc1)cccc6)c2c3c(ccc2P(c5ccc(cc5)C)c4ccc(cc4)C)cccc3
• InChI: 1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3
• InChI key: IOPQYDKQISFMJI-UHFFFAOYSA-N

Description

Application

Takasago Ligands and Complexes for Asymmetric Reactions

(S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO₃, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.

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