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(S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl
[CAS# 100165-88-6]

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Complete supplier list of (S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl
Identification
Classification Chemical reagent >> Organic reagent >> Polycyclic compound
Name (S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl
Synonyms (S)-(-)-2,2'-Bis[di(p-tolyl)phosphino]-1,1'-binaphthyl; (S)-4-Me-BINAP; (S)-Tol-BINAP; 1,1'-(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[1,1-bis(4-methylphenyl)phosphine
Molecular Structure CAS # 100165-88-6, (S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl, (S)-(-)-2,2'-Bis[di(p-tolyl)phosphino]-1,1'-binaphthyl, (S)-4-Me-BINAP, (S)-Tol-BINAP, 1,1'-(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[1,1-bis(4-methylphenyl)phosphine
Molecular Formula C48H40P2
Molecular Weight 678.79
CAS Registry Number 100165-88-6
EC Number 623-900-0
SMILES CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=C(C=C7)C)C8=CC=C(C=C8)C
Properties
Boiling Point 255-257 ºC
Boiling Point 754.4±60.0 ºC (760 mmHg), Calc.*
Flash Point 438.8±39.2 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Self-heating substances or mixturesSelf-heat.2H252
Flammable solidsFlam. Sol.2H228
SDS Available
up Discovory and Applicatios
(S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl, commonly referred to as (S)-BINAP, is a pivotal chiral ligand in asymmetric catalysis. This compound has played a crucial role in the development of highly enantioselective processes, making it a cornerstone in the field of organic synthesis.

The discovery of (S)-BINAP dates back to the 1980s when it was first synthesized by the research group of Ryoji Noyori, a Nobel laureate in Chemistry. Noyori and his team were investigating ways to improve the selectivity and efficiency of chiral catalysts used in asymmetric hydrogenation reactions. Their efforts led to the creation of (S)-BINAP, a compound that quickly gained recognition for its outstanding performance as a chiral ligand.

Structurally, (S)-BINAP consists of a binaphthyl backbone with two bis(4-methylphenyl)phosphino groups attached at the 2,2' positions. This unique structure imparts significant steric hindrance and electronic properties to the ligand, which are crucial for its effectiveness in catalysis. The chiral nature of (S)-BINAP enables it to induce asymmetry in catalytic reactions, leading to the production of enantiomerically pure compounds.

One of the most prominent applications of (S)-BINAP is in asymmetric hydrogenation, where it serves as a ligand for transition metal catalysts, particularly rhodium and ruthenium complexes. These catalytic systems have been employed in the synthesis of various chiral molecules, including pharmaceuticals, agrochemicals, and fine chemicals. The high enantioselectivity achieved with (S)-BINAP-based catalysts has made it possible to produce enantiopure compounds on an industrial scale.

In addition to asymmetric hydrogenation, (S)-BINAP has found applications in other asymmetric catalytic processes, such as allylic substitution, hydroboration, and cyclopropanation reactions. Its versatility as a chiral ligand has made it a valuable tool in the toolbox of synthetic chemists, enabling the efficient synthesis of a wide range of chiral molecules.

The impact of (S)-BINAP on the field of asymmetric catalysis cannot be overstated. It has not only facilitated the development of new catalytic processes but also contributed to the advancement of green chemistry by enabling more sustainable and efficient synthetic methods. The success of (S)-BINAP has inspired the design and synthesis of numerous other chiral ligands, further expanding the possibilities of asymmetric catalysis.

In summary, the discovery of (S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl has been a milestone in the field of asymmetric catalysis. Its application as a chiral ligand has revolutionized the synthesis of enantiopure compounds, making it an indispensable tool in both academic research and industrial production.
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