Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

693030

Sigma-Aldrich

(S)-T-BINAP

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

functional group

phosphine

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCS4679
MKCJ9472
MKCF0624
MKBW2570V
MKBP3295V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
New palladium (II)-catalyzed asymmetric 1, 2-dibromo synthesis
El-Qisairi, Arab K., et al.
Organic Letters, 5.4, 439-441 (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)
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)
View All Related Papers

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

Takasago Ligands

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service