76189-55-4

  • Product Name(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
  • Molecular FormulaC44H32P2
  • Molecular Weight622.7
  • Purity99%
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Product Details

Quick Details

  • CasNo: 76189-55-4
  • Molecular Formula: C44H32P2
  • Purity: 99%

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 76189-55-4 Specifications Powder

  • Molecular Formula:C44H32P2
  • Molecular Weight:622.686
  • Appearance/Colour:white to light yellow crystal powder 
  • Melting Point:239-242 °C 
  • Refractive Index:235 ° (C=0.3, Toluene) 
  • Boiling Point:724.3 °C at 760 mmHg 
  • Flash Point:419 °C 
  • PSA:27.18000 
  • LogP:10.92580 

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(Cas 76189-55-4) Usage

Reaction

(R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester. Useful ligand in asymmetric Heck processes. Ligand employed in palladium-catalyzed asymmetric arylation of ketones. Ligand employed in rhodium-catalyzed 1,4-additions to enones. Ligand employed in palladium-catalyzed hydroamination of styrene derivatives. Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction. Ligand employed in rhodium-catalyzed kinetic resolution of enynes. Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes. Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers. Ligand employed in palladium-catalyzed synthesis of chiral allenes. Ligand for palladium-catalyzed enantioselective hetero Michael addition to form b-amino acid derivatives. Ligand employed in rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols. Ligand employed in rhodium-catalyzed 1,2-addition of aluminium organyl compounds to cyclic enones. Ligand employed in iridium-catalyzed transfer hydrogenative allylation of benzylic alcohols. Ligand employed in rhodium-catalyzed asymmetric C-Si bond formation by conjugate silyl transfer using a Si-B linkage. Ligand employed in the iridium-catalyzed asymmetric cyclopropane-mediated carbonyl allylation of primary alcohols. Ligand employed in the nickel-catalyzed asymmetric α-arylation of tetralones. Ligand employed in the copper-catalyzed asymmetric propargylation of ketones. Ligand employed in the cobalt-catalyzed asymmetric reductive coupling of alkynes with alkenes. Ligand employed in the rhodium-catalyzed asymmetric 1,4-addition of arylalanes on trisubstituted enones. Ruthenium-catalyzed asymmetric hydrocyanation of imines. Palladium-catalyzed asymmetric intermolecular cyclization.

Chemical Properties

white to light yellow crystal powde

Uses

Chiral ligand for metal mediated asymmetric catalysis.

General Description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

 

76189-55-4 Relevant articles

The Trityl-Cation Mediated Phosphine Oxides Reduction

Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric

supporting information, p. 3035 - 3043 (2021/05/10)

Reduction of phosphine oxides into the c...

One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP

Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao

supporting information, (2021/11/18)

Herein reported is the convenient and ef...

Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene

-

, (2020/09/12)

The invention relates to a synthesis met...

Synthetic method of 2,2'-double diphenyl phosphine-1,1'-dinaphthalene

-

Paragraph 0018; 0033; 0034, (2018/10/11)

The invention discloses a synthetic meth...

76189-55-4 Process route

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene
130164-89-5,94041-16-4,94041-18-6,86632-33-9

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With trichlorosilane; triethyl phosphite; In tetrahydrofuran; toluene; at 100 ℃; for 3h;
95%
With 1,3-diphenyl-disiloxane; In toluene; at 110 ℃; chemoselective reaction; Sealed tube;
94%
2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene; With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate; In toluene; at 85 ℃; for 20h;
With sodium hydroxide; water; In toluene; for 0.25h; Product distribution / selectivity;
91%
2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene; With trityl tetrakis(pentafluorophenyl)borate; In (2)H8-toluene; at 20 ℃; Glovebox; Inert atmosphere;
With phenylsilane; In (2)H8-toluene; at 100 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;
23%
With [AlH3(triethylamine)]; In hexane; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;
96 %Chromat.
2,2'-bis(diphenyloxyphosphino)-1,1'-binaphthyl
1227058-20-9

2,2'-bis(diphenyloxyphosphino)-1,1'-binaphthyl

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With tributylphosphine; iodine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;
92%

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