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693030

Sigma-Aldrich

(S)-T-BINAP

Synonym(s):

(S)-(−)-2,2′-p-tolyl-phosphino)-1,1′-binaphthyl, (S)-Tol-BINAP

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About This Item

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
A novel direct catalytic asymmetric synthesis of cyclic indole derivatives by intramolecular carbopalladation of allenes and subsequent intramolecular amination
Hiroi, Kunio, et al.
Tetrahedron Asymmetry, 13.13, 1351-1353 (2002)
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)
New palladium (II)-catalyzed asymmetric 1, 2-dibromo synthesis
El-Qisairi, Arab K., et al.
Organic Letters, 5.4, 439-441 (2003)
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Articles

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Takasago Ligands

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

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