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76189-56-5

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76189-56-5 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.

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 76189-56-5 differently. You can refer to the following data:
1. Reactant involved in:Enantioselective and diastereoselective unpoled carbonyl allylationSyntehsis of organophophine oxides as anittumor agentsSN2 halogenation of hydroxy groupsSynthesis of BINAP complexesStudies of conformational flexibility of BINAP chelates
2. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.

Check Digit Verification of cas no

The CAS Registry Mumber 76189-56-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,1,8 and 9 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 76189-56:
(7*7)+(6*6)+(5*1)+(4*8)+(3*9)+(2*5)+(1*6)=165
165 % 10 = 5
So 76189-56-5 is a valid CAS Registry Number.

76189-56-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (B1405)  (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl  >98.0%(GC)

  • 76189-56-5

  • 1g

  • 750.00CNY

  • Detail
  • TCI America

  • (B1405)  (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl  >98.0%(GC)

  • 76189-56-5

  • 5g

  • 2,880.00CNY

  • Detail
  • Alfa Aesar

  • (B23872)  (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 97%   

  • 76189-56-5

  • 0.25g

  • 345.0CNY

  • Detail
  • Alfa Aesar

  • (B23872)  (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 97%   

  • 76189-56-5

  • 1g

  • 1012.0CNY

  • Detail
  • Alfa Aesar

  • (B23872)  (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 97%   

  • 76189-56-5

  • 5g

  • 4034.0CNY

  • Detail
  • Aldrich

  • (693057)  (S)-BINAP  

  • 76189-56-5

  • 693057-100MG

  • 318.24CNY

  • Detail
  • Aldrich

  • (693057)  (S)-BINAP  

  • 76189-56-5

  • 693057-500MG

  • 875.16CNY

  • Detail
  • Aldrich

  • (295825)  (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene  97%

  • 76189-56-5

  • 295825-250MG

  • 472.68CNY

  • Detail
  • Aldrich

  • (295825)  (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene  97%

  • 76189-56-5

  • 295825-1G

  • 1,137.24CNY

  • Detail
  • Aldrich

  • (295825)  (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene  97%

  • 76189-56-5

  • 295825-5G

  • 4,299.75CNY

  • Detail
  • Sigma-Aldrich

  • (14798)  (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene  puriss.

  • 76189-56-5

  • 14798-100MG

  • 535.86CNY

  • Detail
  • Sigma-Aldrich

  • (14798)  (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene  puriss.

  • 76189-56-5

  • 14798-500MG

  • 992.16CNY

  • Detail

76189-56-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

1.2 Other means of identification

Product number -
Other names BINAP

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:76189-56-5 SDS

76189-56-5Relevant articles and documents

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 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.).

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

-

, (2020/09/12)

The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.

Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane

Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.

supporting information, p. 14434 - 14438 (2017/10/23)

Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.

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