(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨CAS 98327-87-8

(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨CAS 98327-87-8
Product Introduction:
Catalog No.: SS028362
CAS No.: 98327-87-8
Purity(HPLC): 99.5%min
Product Name: (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl
Molecular Formula: C44H32P2
Molecular Weight: 622.68
Synonym(s): 2,2-Bis(diphenylphosphino)-1,1-binaphthyl; (+/-)-BINAP
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Technical Parameters
Description

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Specifications of (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8

 

Property

Value

Appearance

Off-white solid

Purity

99.5% min (HPLC)

Melting Point (MP)

283.0~286.0°C

31P-NMR

Sharp signals, min. 99% area

1H-NMR

Sharp signals, conforming to structure

Introduction

 

(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8 is a bidentate ligand commonly used in organometallic chemistry and catalysis. This compound contains a binaphthyl backbone, which is substituted at the 2,2 positions with two diphenylphosphino groups. The molecule exhibits chirality due to the binaphthyl structure, making it useful in asymmetric catalysis, especially in reactions requiring chiral catalysts.
Production:
This compound is synthesized by the reaction of 1,1-binaphthyl with diphenylphosphine in the presence of suitable reagents or catalysts to form the bidentate ligand. The resulting ligand is then purified and isolated for use in catalytic processes.

 

Applications of (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8

 

1.Asymmetric Catalysis:
oThe primary application of (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl is in asymmetric catalysis. It is widely used as a ligand in transition metal catalysis to induce chirality in reactions. In particular, it is used in reactions like hydrogenation, cross-coupling, and oxidative coupling. The chiral environment created by this ligand helps in the formation of enantiomerically enriched products, which are essential in the synthesis of pharmaceuticals and fine chemicals.
2.Catalyst for Metal-Catalyzed Reactions:
o(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8 is frequently paired with transition metals like palladium, rhodium, and iridium to create highly efficient catalysts. These metal-ligand complexes are used in a variety of important reactions, including:
Suzuki-Miyaura coupling (a palladium-catalyzed cross-coupling reaction for carbon-carbon bond formation)
Hiyama coupling (a silicon-carbon bond-forming reaction)
Hydroformylation (the conversion of alkenes to aldehydes)
Hydrogenation reactions (for selective hydrogenation of unsaturated compounds).
3.Synthesis of Chiral Compounds:
oThe use of (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl as a ligand allows for the synthesis of chiral compounds. The ability of this ligand to induce chirality in catalytic processes makes it invaluable in the preparation of optically active molecules, which are crucial in the pharmaceutical and agrochemical industries.
4.Applications in Organometallic Chemistry:
oThis ligand is used to form stable organometallic complexes. Its ability to coordinate to metals through the phosphine groups enhances the stability and reactivity of the metal center. The resulting metal-ligand complexes can be used in a range of reactions, including hydroformylation, oxidation, and reduction reactions.
5.Precursor for Other Ligands:
o(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8 can be used as a precursor in the synthesis of other bidentate and chiral ligands. These ligands are useful in a variety of metal-catalyzed reactions, and their versatility makes them important tools in synthetic chemistry.

 

Conclusion

 

(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl丨98327-87-8 is a widely used bidentate ligand in asymmetric catalysis and organometallic chemistry. Its ability to induce chirality and form stable complexes with transition metals makes it invaluable in synthetic chemistry, particularly in the creation of enantiomerically pure compounds. Through its role as a catalyst or catalyst modifier, it is integral to numerous industrial and pharmaceutical applications.

 

 

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