97764-56-2

Basic information

• Product Name: (S_P,S_P)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane
• CAS NO: 97764-56-2
• Molecular Weight: 486.146
• Mol File: 97764-56-2.mol

Chemical Properties

• CAS DataBase Reference: (S_P,S_P)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane(CAS DataBase Reference)
• NIST Chemistry Reference: (S_P,S_P)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane(97764-56-2)
• EPA Substance Registry System: (S_P,S_P)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane(97764-56-2)

Safety Data

• Hazardous Substances Data: 97764-56-2(Hazardous Substances Data)

Upstream product

• 1316041-04-9 C₂₆H₃₀B₂O₂P₂ 
• 74-88-4 methyl iodide 
• 578-57-4 2-bromoanisole 
• 1155850-63-7 (R_P,R_P)-1,2-bis[(methoxy)(phenyl)phosphino-P-borane]ethane 
• 127687-02-9 (S)-o-anisyl(2-iodoethyl)phenylphosphine-borane 
• 97764-41-5 (S)-(+)-(o-anisyl)(methyl)phenylphosphine/borane complex 
• 14044-65-6 borane-THF 
• 55739-59-8 (1R,1R')-(-)-1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide 
• 19315-13-0 methyl(phenyl)phosphineoxide 
• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 1316041-04-9 (R_P,R_P)-1,2-bis[(o-hydroxyphenyl)(phenyl)phosphino-P-borane]ethane 

Downstream Products

• 55739-58-7 (R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane 
• 55739-58-7 (S(P),S(P))-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane 
• 917029-49-3 (R_P,R_P)-1,2-bis[(phenyl)(2-triisopropylsiloxyphenyl)phosphino-P-borane]ethane 
• 1316041-11-8 (R_P,R_P)-1,2-bis{[2-(N-tert-butylcarbamoylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 917029-53-9 (R_P,R_P)-1,2-bis{[2-(tert-butoxycarbonylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 917029-52-8 (R_P,R_P)-1,2-bis{[2-(9-anthrylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 81964-01-4 (R_P,R_P)-1,2-bis[(o-hydroxyphenyl)(phenyl)phosphino]ethane 
• 1316041-35-6 (R_P,R_P)-1,2-bis[(2-(diphenylphosphinyloxy)phenyl)(phenyl)phosphino]ethane 
• 1316041-34-5 (R_P,R_P)-1,2-bis{(phenyl)[2-(p-tosyloxy)phenyl]phosphino}ethane 
• 1316041-31-2 (R_P,R_P)-1,2-bis[(2-benzoyloxyphenyl)(phenyl)phosphino]ethane 
• 917029-70-0 (R_P,R_P)-1,2-bis[(phenyl)(2-pivaloyloxyphenyl)phosphino]ethane 
• 81964-02-5 (R_P,R_P)-1,2-bis[(2-acetoxyphenyl)(phenyl)phosphino]ethane 
• 917029-71-1 (R_P,R_P)-1,2-bis[(phenyl)(2-triisopropylsiloxyphenyl)phosphino]ethane 
• 1316041-28-7 (R_P,R_P)-1,2-bis{[2-(N-tert-butylcarbamoylmethoxy)phenyl](phenyl)phosphino}ethane 

Relevant articles and documents

P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides

The development of transition-metal-catalyzed methods for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Herein, we present a direct Pd/Xiao-Phos-catalyzed cross-coupling reaction of easily accessible secondary phosphine o

Profiling the tuneable R-SMS-Phos structure in the rhodium(i)-catalyzed hydrogenation of olefins: The last stand?

A diversified family of enantiopure P-stereogenic "R-SMS-Phos" {R-SMS-Phos = 1,2-bis[(o-RO-phenyl)(phenyl)phosphino]ethane} ligands wherein R = branched or heteroatom-substituted alkyl, aralkyl, silyl, acyl, sulfonyl, etc. was screened for the Rh(i)-catalyzed hydrogenation of a representative set of olefinic substrates. This systematic and detailed investigation revealed a marked beneficial impact on enantioselectivity and catalyst activity in comparison to Knowles' ultimate DiPAMP {DiPAMP = 1,2-bis[(o-anisyl)(phenyl) phosphino]ethane} design. Mutant ligands with highly enhanced properties possessing particular features wherein the DiPAMP structure is found embedded were identified. The Royal Society of Chemistry 2011.

Impact of incorporating substituents onto the P-o-anisyl groups of DiPAMP ligand on the rhodium(I)-catalyzed asymmetric hydrogenation of olefins

The introduction of 1,2-bis[(o-anisyl)-(phenyl)phosphino]ethane (DiPAMP) as a P-stereogenic ligand for rhodium(I)-catalyzed hydrogenation by Knowles et al. came after their evaluation of several diphosphines. However, no in-depth study was carried out on incorporating various substituents on its P-o-anisyl groups. In this work, we have prepared a large series of enantiopure and closely related DiPAMP analogues possessing various substituents (MeO, TMS, t-Bu, Ph, fused benzene ring) on the o-anisyl rings. The new ligands were evaluated in rhodium-catalyzed hydrogenation of several model substrates: methyl α-acetamidoacrylate, methyl (Z)-α-acetamidocinnamate, methyl (Z)-β-acetamidocrotonate, dimethyl itaconate, and atropic acid. They displayed enhanced activities and increased enantioselectivities, particularly the P-(2,3,4,5-tetra-MeO-C6H)-substituted ligand (4MeBigFUS). Interestingly enough, 88% ee was obtained in the hydrogenation of atropic acid using the Rh-(4MeBigFUS) catalyst under mild conditions (10 bar H2, room temperature) versus 7% ee using Rh-DiPAMP. Conversely, the ligand possessing P-(2,6-di-MeO-C6H3) groups proved to slow down considerably the hydrogenation. X-Ray structures of their corresponding Rh complexes are presented and discussed.

Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes

Secondary and tertiary phosphine-boranes were synthesized in one-pot from phosphine oxides or substituted chlorophosphines without isolation of the intermediate phosphines. Phosphine-boranes having a methyl group were metalated with sec-butyllithium. The generated carbanions reacted with alkyl halides or carbonyl compounds to yield various phosphine-borane derivatives. The carbanions underwent copper(II)-promoted oxidative coupling without impairment of the borane functionality. Secondary phosphine-boranes reacted with alkyl halides, aldehydes, or α,β-unsaturated carbonyl compounds to give phosphine-borane derivatives having a functional group. The boranato group of phosphine-boranes was removed in a stereospecific manner with retention of configuration by treatment with a large excess of amine such as morpholine. A new route to bidentate ligands with homochiral phosphine centers has been explored by utilizing these characteristic reactivities of phosphine-boranes. Thus, optically pure (S,S)-1,2-bis(o-anisylphenylphosphino)ethane, (R,R)-1,2-bis(tert-butylphenyl-phosphino)ethane, and (S,S)-1,4-bis(o-anisylphenylphosphino)butane have been synthesized via phosphine-boranes.