• 1. Highly enantioselective Cu(i)–Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters
  Shun-Yi Wang,Teck-Peng Loh Chem. Commun. 2010 46 8694
• 2. Highly enantioselective Cu(i)–Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters
  Shun-Yi Wang,Teck-Peng Loh Chem. Commun. 2010 46 8694
• 3. Catalytic asymmetric transformations of oxa- and azabicyclic alkenes
  Sundaravel Vivek Kumar,Andy Yen,Mark Lautens,Patrick J. Guiry Chem. Soc. Rev. 2021 50 3013
• 4. Iron-catalyzed thioetherification of thiols with aryl iodides
  Jhih-Ru Wu,Che-Hung Lin,Chin-Fa Lee Iron-catalyzed thioetherification of thiols with aryl iodides. Jhih-Ru Wu Che-Hung Lin Chin-Fa Lee Chem. Commun. 2009 4450
• 5. Synthesis of novel chiral ruthenium complexes of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and their use as asymmetric catalysts
  Takao Ikariya,Youichi Ishii,Hiroyuki Kawano,Tsuneta Arai,Masahiko Saburi,Sadao Yoshikawa,Susumu Akutagawa J. Chem. Soc. Chem. Commun. 1985 922

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylphosphines and derivatives

The Comprehensive Overview of (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl (CAS No. 100165-88-6)

(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, commonly referred to as BINAP or its full name Binaphthyl derivative, is a chiral ligand widely utilized in asymmetric catalysis and organometallic chemistry. This compound, with the CAS registry number 100165-88-6, has garnered significant attention due to its unique structure and versatile applications in modern chemical research.

The synthesis of this compound involves a multi-step process, typically starting from binaphthyl derivatives and subsequent functionalization with di-p-tolylphosphine groups. The stereochemistry of the molecule is crucial, as the (S) configuration imparts specific chiral properties essential for its catalytic activity. Recent advancements in asymmetric synthesis have further optimized the production of this compound, ensuring high enantiomeric purity and scalability for industrial applications.

BINAP is renowned for its role in asymmetric hydrogenation reactions, particularly in the Noyori asymmetric hydrogenation of ketones. This ligand's ability to induce high enantioselectivity has made it indispensable in the production of chiral pharmaceutical intermediates and fine chemicals. Recent studies have explored its application in more complex systems, such as tandem catalytic processes and enantioselective cyclopropanation reactions.

In terms of structural characterization, BINAP exhibits a rigid binaphthyl backbone with two di-p-tolylphosphine substituents at the 2-position of each naphthyl ring. This arrangement creates a chiral pocket capable of coordinating transition metals like rhodium and ruthenium with high selectivity. Advanced techniques such as X-ray crystallography and computational modeling have provided deeper insights into the molecular geometry and its influence on catalytic performance.

The optical properties of this compound are also a subject of interest, particularly in materials science applications. Research into its use as a chiral selector in liquid crystals and self-assembled monolayers has revealed promising results for potential applications in optoelectronics and sensor technologies.

Recent breakthroughs in sustainable chemistry have highlighted the eco-friendly aspects of using BINAP-based catalysts. For instance, their application in biomass conversion processes offers a green alternative to traditional methods, aligning with global efforts to reduce environmental impact.

In conclusion, (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl stands as a testament to the ingenuity of modern chemical synthesis and catalysis. Its continued exploration across diverse fields underscores its significance as a cornerstone ligand in contemporary chemical research.

• 76189-56-5((S)-BINAP)
• 135139-00-3((S)-(-)-2,2'-Bisdi-(3,5-dimethylphenyl)phosphino-1,1'-binaphthyl)
• 145416-77-9(rac-2,2 -Bis(di(3,5-dimethylphenyl)phosphino)-1,1 -binaphthyl)
• 405919-42-8
• 915695-20-4(PHOSPHINE, [1,1'-BINAPHTHALEN]-2-YLBIS(2-METHYLPHENYL)-)
• 76189-55-4((R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)
• 137219-86-4((R)-(+)-XylBINAP)
• 153305-67-0(2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL)
• 98327-87-8(1.1'-Binaphthyl-2.2'-diphemyl phosphine)
• 99646-28-3((R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl)