(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
[CAS# 98327-87-8]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
• Synonyms: 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (+/-)-BINAP
• Molecular Formula: C₄₄H₃₂P₂
• Molecular Weight: 622.68
• CAS Registry Number: 98327-87-8
• EC Number: 619-338-0
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8

Properties

• Melting point: 280-285 °C
• alpha: 20

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H410-H413
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

The discovery of (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, known as BINAP, marks a significant milestone in the field of catalysis and asymmetric synthesis. This compound, with its distinct binaphthyl framework and two diphenylphosphino groups, has revolutionized the way chemists approach the synthesis of chiral molecules.

BINAP emerged in the late 20th century and quickly gained prominence due to its unique structural features. The binaphthyl backbone, combined with the steric hindrance provided by the diphenylphosphino groups, creates a chiral environment that is highly effective in asymmetric reactions. This chiral environment is crucial for facilitating reactions that produce optically active compounds, which are essential in a wide range of applications, from pharmaceuticals to advanced materials.

The primary application of BINAP lies in catalytic asymmetric synthesis, where it serves as a ligand for transition metals such as rhodium and palladium. These metal-ligand complexes, also known as chiral catalysts, enable reactions that yield enantiomerically pure substances. The ability to produce such high-purity chiral products is of paramount importance in the pharmaceutical industry, where the efficacy and safety of drugs often depend on the precise arrangement of their chiral centers.

One of the most notable contributions of BINAP is in the asymmetric hydrogenation of prochiral ketones and alkenes. This process is essential for generating enantiomerically pure substances with high efficiency and selectivity. BINAP's role in this reaction has significantly improved the production of chiral molecules, making the synthesis of complex drugs and other fine chemicals more streamlined and cost-effective.

Beyond its applications in pharmaceuticals, BINAP has also influenced the development of specialized materials. Its use in creating chiral materials extends to fields such as electronics and renewable energy technologies, where the precision and efficiency of BINAP-based catalysts play a crucial role. The innovation spurred by BINAP has led to further advancements in ligand design, resulting in the creation of new compounds with enhanced specificity and utility in catalysis.

The impact of BINAP on chemical synthesis is profound. It has not only enhanced the precision of asymmetric synthesis but also opened new avenues for research and development in various industries. The ongoing exploration of BINAP and its derivatives continues to drive progress in both academic and industrial settings, underscoring the transformative power of this remarkable compound in the field of chemistry.

References

2024. Rh-catalysed enantioselective [2+2+1] cycloaddition reactions using three different 2π-components. Nature Synthesis, 3(7).
DOI: 10.1038/s44160-024-00604-7

2024. Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates. Science China Chemistry, 67(2).
DOI: 10.1007/s11426-023-1922-5

2024. Catalytic atroposelective synthesis. Nature Catalysis, 7(4).
DOI: 10.1038/s41929-024-01138-z