(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL, CAS No. 100165-88-6

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100165-88-6

Catalog No. EBD3039827

CAS 100165-88-6

Name (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

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Basic Information

Synonyms: (S)-T-BINAP (R)-TOL-BINAP (S)-TOL-BINAP (S)-4-ME-BINAP 98%(S)-TOLBINAP BISDIPTOLYLPHOSPHINOBINAPHTHYLSTOLBI (S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-& (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 1,1'-binaphthalene-2,2'-diylbis[bis(4-methylphenyl)phosphane] (S)-(-)-TolBINAP (S)-TolBINAP

Molecular Formula: C48H40P2

Molecular Weight: 678.78

Categories: Materials Chemistry > Optoelectronic and Organic Semiconductor Materials > Optoelectronic Functional Compounds Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

Product Description:

(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, commonly abbreviated as (S)-Tol-BINAP, is a chiral bisphosphine ligand. It is a derivative of the well-known BINAP ligand, where the phenyl groups on the phosphorus atoms are replaced by p-tolyl groups. This modification can influence its electronic and steric properties, as well as its solubility in various reaction media. (S)-Tol-BINAP is primarily employed as a chiral ligand in transition metal-catalyzed asymmetric synthesis. It forms complexes with metals like ruthenium (Ru), rhodium (Rh), and palladium (Pd) to create highly efficient catalysts for a variety of enantioselective transformations. Key applications include asymmetric hydrogenation of olefins, ketones, and imines, which are crucial steps in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. Its role is to induce chirality in the product by providing a well-defined chiral environment around the catalytic metal center. Compared to BINAP, the p-tolyl substituents in Tol-BINAP can offer advantages such as enhanced catalyst stability or modified reactivity/selectivity profiles in specific reactions. It is a valuable tool in both academic research and industrial process development for accessing enantiomerically pure compounds.

Physical Properties

Melting Point: 252-256 °C

Boiling Point: 754.4 °C at 760 mmHg

Flash Point: 438.8 °C

Analytical Data

Appearance: White powder