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Sigma-Aldrich

(S)-T-BINAP

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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
PubChem Substance ID:
329761556
NACRES:
NA.22

form

solid

Quality Level

100

optical activity

[α]20/D -156°, c = 0.5 in benzene

mp

250-255 °C

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

Related Categories

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.

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

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An enantioselective Baylis?Hillman reaction catalyzed by chiral phosphines under atmospheric pressure
Hayase, Tadakatsu, et al.
Chemical Communications (Cambridge, England), 12, 1271-1272 (1998)
Asymmetric synthesis of a-aminoamides by Pd-catalyzed double carbohydroamination.
Nanayakkara P and Alper H.
Chemical Communications (Cambridge, England), 18, 2384-2385 (2003)
Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline
Overman, Larry E., and Emily A. Peterson
Angewandte Chemie (International Edition in English), 42.22, 2525-2528 (2003)
Catalytic enantioselective hydroboration of cyclopropenes
Rubina, Marina, Michael Rubin, and Vladimir Gevorgyan
Journal of the American Chemical Society, 125.24, 7198-7199 (2003)
Highly Efficient Copper (I) Iodide?Tolyl?BINAP?Catalyzed Asymmetric Conjugate Addition of Methylmagnesium Bromide to ?, ??Unsaturated Esters
Wang, Shun?Yi, et al.
Advanced Synthesis & Catalysis, 350.5, 673-677 (2008)
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Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

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