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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:
Molecular Weight:
678.78
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

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

Application

(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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Parallel kinetic resolution of 4-alkynals catalyzed by Rh (I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones
Tanaka Ken and Gregory C.Fu
Journal of the American Chemical Society, 125.27, 8078-8079 (2003)
Asymmetric synthesis of a-aminoamides by Pd-catalyzed double carbohydroamination.
Nanayakkara P and Alper H.
Chemical Communications (Cambridge, England), 18, 2384-2385 (2003)
An enantioselective Baylis?Hillman reaction catalyzed by chiral phosphines under atmospheric pressure
Hayase, Tadakatsu, et al.
Chemical Communications (Cambridge, England), 12, 1271-1272 (1998)
Catalytic enantioselective hydroboration of cyclopropenes
Rubina, Marina, Michael Rubin, and Vladimir Gevorgyan
Journal of the American Chemical Society, 125.24, 7198-7199 (2003)
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)

Articles

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

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

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