86632-33-9

Basic information

• Product Name: PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS
• Synonyms: PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS
• CAS NO: 86632-33-9
• Molecular Formula: C₄₄H₃₂O₂P₂
• Molecular Weight: 654.67
• Mol File: 86632-33-9.mol

Chemical Properties

• Melting Point: 293-295 °C (decomp)
• Boiling Point: 864.8±65.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• CAS DataBase Reference: PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS(CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS(86632-33-9)
• EPA Substance Registry System: PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS(86632-33-9)

Safety Data

• Hazardous Substances Data: 86632-33-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS is used as a ligand in asymmetric catalysis for the production of pharmaceuticals. Its rigid, chiral structure allows for precise control of the stereochemistry of reactions, leading to the synthesis of complex molecules with high selectivity and efficiency.
Used in Fine Chemicals Industry:
In the fine chemicals industry, PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS is employed as a catalyst in various chemical reactions. Its ability to bind to metal ions and assist in reactions makes it a valuable tool for the synthesis of high-quality fine chemicals with specific stereochemical properties.
Used in Organic Synthesis:
PHOSPHINE OXIDE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS is utilized as a catalyst in organic synthesis to facilitate a wide range of chemical reactions. Its unique structure and ability to bind to metal ions make it an effective tool for achieving high levels of selectivity and efficiency in the synthesis of complex organic molecules.

Upstream product

• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 1499-21-4 Diphenylphosphinic chloride 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 130164-89-5 2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 2743-38-6 O,O'-dibenzoyl-L-tartaric acid 
• 1079-66-9 chloro-diphenylphosphine 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 

Downstream Products

• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 86632-33-9 (R)-2,2’-bis(1,1-diphenyl-1,1’-phosphine oxide)-1,1’-binaphthyl 
• 86632-33-9 (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide) 
• 597578-38-6 11-phenylbenzo[b]dinaphtho[2,1-d:1’,2’-f]phosphepine-1 1-oxide 
• 597578-44-4 2,2'-bis[phenyl(2-trimethylsilylphenyl)phosphinoyl]-1,1'-binaphthyl 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 
• 681244-37-1 5,5'-dibromoBINAPO 
• 1746-13-0 allyl phenyl ether 
• 868140-13-0 4,4'-dibromo-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) dioxide 
• 847864-32-8 Eu(4,4,4-trifluoro-1-(2-napthyl)-1,3-butanedione)3(1,1'-binaphthyl phosphine oxide) 

Relevant articles and documents

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Chiral Recognition of in Situ-Oxidized Phosphine Oxides with Octahedral Indium Complexes by 31P NMR Spectroscopy

Herein, efficient chiral recognition of phosphine oxides with octahedral indium complexes was demonstrated. Direct chiral analysis of in situ-prepared phosphine oxides formed using phosphines and hydrogen peroxide was conducted effectively via 31P nuclear magnetic resonance spectroscopy. Sufficient peak resolution of chiral phosphines was obtained consistently, thereby enabling the reliable determination of absolute chirality. Rational 1:1 binding models based on experiments and density functional theory calculations have been proposed.

Photoresponsive Propeller-like Chiral AIE Copper(I) Clusters

A pair of propeller-like chiral trinuclear CuI clusters (R/S-Cu3) with unique photoinduced fluorescence enhancement were prepared. R/S-Cu3 showed intense variable luminescence after UV light irradiation, which was attributed to the stepwise oxidation of ligand in the clusters. It exhibited typical aggregation-induced emission (AIE) (αAIE=17.3). Mechanism studies showed that metal cluster-centered (MCC) and triplet metal-to-ligand charge-transfer (3MLCT) processes are the origin of the luminescence; the processes are regulated by a restriction of intramolecular motions mechanism in a different state. The chiral structure and AIE feature endow R/S-Cu3 with remarkable circularly polarized luminescence (glum=2×10?2) in the aggregated state. It shows good capability for producing reactive oxygen species. This work enriches the kinds of atomically precise AIE clusters, gains insight into their luminescence mechanism, and offers the prospect of application in multifunctional materials.

Circularly polarized luminescence of Sm (III) and Eu (III) complexes with chiral ligand (R/S)-BINAPO

Luminescent lanthanide (III) ions have been exploited for circularly polarized luminescence (CPL) for decades. However, very few of these studies have involved chiral samarium (III) complexes. Complexes are prepared by mixing axial chiral ligands (R/S))-2

Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines

A series of bifunctional phosphine oxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asymmetric hydrosilylation of ketimines. bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide displayed the highest enantioselectivity of 60%.

An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide-iron(ii) complexes

An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(ii)-diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS suggest that a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is a pre-catalyst for a Fe(iii)/Fe(iv) redox cycle.

Porous Rh/BINAP polymers as efficient heterogeneous catalysts for asymmetric hydroformylation of styrene: Enhanced enantioselectivity realized by flexible chiral nanopockets

A new chiral monomer, (S)-5,5′-divinyl-BINAP, was successfully synthesized and embedded into two different porous organic polymers (Poly-1 and Poly-2). After loading a Rh species, the catalysts were applied for the heterogeneous asymmetric hydroformylation of styrene. Compared with the homogeneous BINAP analogue, the enantioselectivity of Rh/Poly-1 catalyst was drastically increased by approximately 70%. The improved enantioselectivity of the porous Rh/BINAP polymers was attributed to the presence of flexible chiral nanopockets resulting from the increased bulk of the R groups near the catalytic center.

Two chiral ligands, and preparation and applications of chiral porous organic polymer

The present invention provides a preparation method of two vinyl BINAP(2,2,-bis(diphenylphosphino)-1,1,-binaphthyl) derivative ligands, a preparation method of a related polymer, and applications of the related polymer as a catalyst carrier in an asymmetr

Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis

Two vinyl-functionalized chiral 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligands, (S)-4,4′-divinyl-BINAP and (S)-5,5′-divinyl-BINAP, were successfully synthesized. Chiral BINAP-based porous organic polymers (POPs), denoted as 4-BINAP@POPs and 5-BINAP@POPs, were efficiently prepared via the copolymerization of vinyl-functionalized BINAP with divinyl benzene under solvothermal conditions. Thorough characterization using nuclear magnetic resonance spectroscopy, thermogravimetric analysis, extended X-ray absorption fine structure analysis, and high-angle annular dark-field scanning transmission electron microscopy, we confirmed that chiral BINAP groups were successfully incorporated into the structure of the materials considered to contain hierarchical pores. Ru was introduced as a catalytic species into the POPs using different synthetic routes. Systematic investigation of the resultant chiral Ru/POP catalysts for heterogeneous asymmetric hydrogenation of β-keto esters revealed their excellent chiral inducibility as well as high activity and stability. Our work thereby paves a path towards the use of advanced hierarchical porous polymers as solid chiral platforms for heterogeneous asymmetric catalysis.

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.