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76189-56-5,MFCD00010805
Catalog No.:AA00ICMZ

76189-56-5 | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00ICMZ
Chemical Name:
(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene
CAS Number:
76189-56-5
Molecular Formula:
C44H32P2
Molecular Weight:
622.6724
MDL Number:
MFCD00010805
SMILES:
c1ccc(cc1)P(c1cc2ccccc2cc1c1c(ccc2c1cccc2)P(c1ccccc1)c1ccccc1)c1ccccc1
Properties
Properties
 
BP:
724.3°C at 760 mmHg  
Form:
Solid  
MP:
283-286 °C(lit.)  
Refractive Index:
-235 ° (C=0.3, Toluene)  
Stability:
Air Sensitive  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
797  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
46  
Rotatable Bond Count:
7  
XLogP3:
11.4  

Downstream Synthesis Route

[1]Wu,Hai-Chen;Yu,Jin-Quan;Spencer,JonathanB.[OrganicLetters,2004,vol.6,#25,p.4675-4678]

[2]Buonomo,JosephA.;Eiden,CarterG.;Aldrich,CourtneyC.[Chemistry-AEuropeanJournal,2017,vol.23,#58,p.14434-14438]

[3]CurrentPatentAssignee:CENTRENATIONALDELARECHERCHESCIENTIFIQUE;SOLVAY-US2008/214857,2008,A1Locationinpatent:Page/Pagecolumn12

[4]Landais,Yannick;Laye,Claire;Lusseau,Jonathan;Robert,Frédéric[AdvancedSynthesisandCatalysis,2021,vol.363,#12,p.3035-3043]

[5]Yang,Shuyan;Han,Xinxin;Luo,Minmin;Gao,Jing;Chu,Wenxiang;Ding,Yuqiang[RussianJournalofGeneralChemistry,2015,vol.85,#5,p.1156-1160][Zh.Obshch.Khim.]

[6]Jin,Hongyu;Gu,Chengshan;Xiao,Zhihuan;Tan,Qihang;Liu,Long;Han,Li-Biao;Chen,Wen-Hao;Chen,Tieqiao[EuropeanJournalofOrganicChemistry,2023,vol.26,#29]

[1]CurrentPatentAssignee:CENTRENATIONALDELARECHERCHESCIENTIFIQUE;SOLVAY-US2007/10695,2007,A1Locationinpatent:Page/Pagecolumn20

[2]Seki,Tomohiro;McEleney,Kevin;Crudden,CathleenM.[ChemicalCommunications,2012,vol.48,#51,p.6369-6371]

[3]Landais,Yannick;Laye,Claire;Lusseau,Jonathan;Robert,Frédéric[AdvancedSynthesisandCatalysis,2021,vol.363,#12,p.3035-3043]

[4]Petersson,MariaJ.;Loughlin,WendyA.;Jenkins,IanD.[ChemicalCommunications,2008,#37,p.4493-4494]

[5]Locationinpatent:experimentalpartHatano,Bunpei;Hashimoto,Kazuyuki;Katagiri,Hiroshi;Kijima,Tatsuro;Murakami,Satoshi;Matsuba,Shigeru;Kusakari,Miho[JournalofOrganicChemistry,2012,vol.77,#7,p.3595-3597]

[6]CurrentPatentAssignee:SAMSUNGSDICO.,LTD.-WO2016/207224,2016,A1Locationinpatent:Page/Pagecolumn20;21

[7]CurrentPatentAssignee:SERVIERMONDE-WO2022/36033,2022,A2Locationinpatent:Paragraph00431;00475-00476

[8]CurrentPatentAssignee:SERVIERMONDE-WO2022/36033,2022,A2Locationinpatent:Paragraph00431;00475-00476

[9]Busacca,CarlA.;Raju,Ravinder;Grinberg,Nelu;Haddad,Nizar;James-Jones,Paul;Lee,Heewon;Lorenz,JonC.;Saha,Anjan;Senanayake,ChrisH.[JournalofOrganicChemistry,2008,vol.73,#4,p.1524-1531]

[10]Locationinpatent:experimentalpartMotoshima,Kosuke;Sato,Akinori;Yorimitsu,Hideki;Oshima,Koichiro[BulletinoftheChemicalSocietyofJapan,2007,vol.80,#11,p.2229-2231]

[11]Locationinpatent:experimentalpartLam,Kim-Hung;Chui,Chung-Hin;Gambari,Roberto;Wong,RaymondSiu-Ming;Cheng,GregoryYin-Ming;Lau,Fung-Yi;Lai,PaulBo-San;Tong,See-Wai;Chan,Kit-Wah;Wong,Wai-Yeung;Chan,AlbertSun-Chi;Tang,JohnnyCheuk-On[EuropeanJournalofMedicinalChemistry,2010,vol.45,#11,p.5527-5530]

[12]Rajendran,KamalrajV.;Gilheany,DeclanG.[ChemicalCommunications,2012,vol.48,#6,p.817-819]

[13]Buonomo,JosephA.;Eiden,CarterG.;Aldrich,CourtneyC.[Chemistry-AEuropeanJournal,2017,vol.23,#58,p.14434-14438]

[14]Jin,Hongyu;Gu,Chengshan;Xiao,Zhihuan;Tan,Qihang;Liu,Long;Han,Li-Biao;Chen,Wen-Hao;Chen,Tieqiao[EuropeanJournalofOrganicChemistry,2023,vol.26,#29]

[1]CurrentPatentAssignee:ROCHEHOLDINGAG-US2003/232825,2003,A1Locationinpatent:Page30

[1]CurrentPatentAssignee:ROCHEHOLDINGAG-US2003/232825,2003,A1Locationinpatent:Page31

[1]CurrentPatentAssignee:ROCHEHOLDINGAG-US2003/232825,2003,A1Locationinpatent:Page31

Literature

Title: rac-2,2'-Bis(diphenyl-phosphan-yl)-1,1'-binaphth-yl: a racemic diphosphine ligand.

Journal: Acta crystallographica. Section E, Structure reports online 20120701

Title: A new cascade reaction: concurrent construction of six and five membered rings leading to novel fused quinazolinones.

Journal: Organic & biomolecular chemistry 20120421

Title: Di-μ-iodido-bis-{[(R)-(+)-2,2'-bis-(di-phenyl-phosphan-yl)-1,1'-binaphthyl-κ(2)P,P']copper(I)} 0.67-hydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20120401

Title: (+)-Chlorido[(1,2,3,4-η;κP)-2'-diphenyl-phosphanyl-2-diphenyl-phosphoryl-1,1'-binaphth-yl]rhodium(I) methanol monosolvate.

Journal: Acta crystallographica. Section E, Structure reports online 20120301

Title: A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates.

Journal: Journal of the American Chemical Society 20110713

Title: Synthesis of α-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack reaction of 3-acetyl-2-chloroindoles.

Journal: Organic letters 20110318

Title: Rhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ-oxo-carboxylic acids by oxidation of the furyl ring with ozone.

Journal: Chemistry, an Asian journal 20110301

Title: Highly enantioselective alkynylation of trifluoropyruvate with alkynylsilanes catalyzed by the BINAP-Pd complex: access to α-trifluoromethyl-substituted tertiary alcohols.

Journal: Organic letters 20101217

Title: Highly enantioselective Cu(I)-Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters.

Journal: Chemical communications (Cambridge, England) 20101214

Title: The preparation of bi-functional organophosphine oxides as potential antitumor agents.

Journal: European journal of medicinal chemistry 20101101

Title: Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction.

Journal: Organic & biomolecular chemistry 20100628

Title: Synthesis, characterization, and catalytic properties of new electrophilic iridium(III) complexes containing the (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl ligand.

Journal: Inorganic chemistry 20100503

Title: Origin of intense chiroptical effects in undecagold subnanometer particles.

Journal: Journal of the American Chemical Society 20100203

Title: Synthesis and characterization of FePd magnetic nanoparticles modified with chiral BINAP ligand as a recoverable catalyst vehicle for the asymmetric coupling reaction.

Journal: Physical chemistry chemical physics : PCCP 20091021

Title: Asymmetric Rh-catalyzed intermolecular hydroacylation of 1,5-hexadiene with salicylaldehyde.

Journal: Chemical & pharmaceutical bulletin 20091001

Title: Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes.

Journal: The Journal of organic chemistry 20090904

Title: N-heterocyclization of naphthylamines with 1,2- and 1,3-diols catalyzed by an iridium chloride/BINAP system.

Journal: The Journal of organic chemistry 20090116

Title: Counterintuitive kinetics in Tsuji-Trost allylation: ion-pair partitioning and implications for asymmetric catalysis.

Journal: Journal of the American Chemical Society 20081105

Title: The hydrogenation/transfer hydrogenation network in asymmetric reduction of ketones catalyzed by [RuCl2(binap)(pica)] complexes.

Journal: Chemistry, an Asian journal 20081006

Title: Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones.

Journal: Organic & biomolecular chemistry 20071107

Title: Conformationally constrained, stable, triplet ground state (S = 1) nitroxide diradicals. Antiferromagnetic chains of S = 1 diradicals.

Journal: Journal of the American Chemical Society 20070822

Title: Synthesis of bulky phosphines by rhodium-catalyzed formal [2+2+2] cycloaddition reactions of tethered diynes with 1-alkynylphosphine sulfides.

Journal: Journal of the American Chemical Society 20070606

Title: Enantioselective hydrogenation of quinolines catalyzed by Ir(BINAP)-cored dendrimers: dramatic enhancement of catalytic activity.

Journal: Organic letters 20070329

Title: Cu(I) Tol-BINAP-catalyzed enantioselective Michael reactions of Grignard reagents and unsaturated esters.

Journal: Journal of the American Chemical Society 20070117

Title: An unexpected possible role of base in asymmetric catalytic hydrogenations of ketones. Synthesis and characterization of several key catalytic intermediates.

Journal: Journal of the American Chemical Society 20061025

Title: Control of optically active structure of thioether-phthalocyanine aggregates by chiral Pd(II)-BINAP complexes in toluene and at the toluene/water interface.

Journal: Chirality 20060801

Title: Chiroptical activity of BINAP-stabilized undecagold clusters.

Journal: The journal of physical chemistry. B 20060622

Title: Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes.

Journal: Journal of the American Chemical Society 20060322

Title: Intramolecular Pd-catalyzed carboetherification and carboamination. Influence of catalyst structure on reaction mechanism and product stereochemistry.

Journal: Journal of the American Chemical Society 20060308

Title: Oxidative addition of phenyl bromide to Pd(BINAP) vs Pd(BINAP)(amine). Evidence for addition to Pd(BINAP).

Journal: Organic letters 20060302

Title: Solution structures and behavior of trans-RuH(eta(1)-BH(4)) (binap)(1,2-diamine) complexes.

Journal: Magnetic resonance in chemistry : MRC 20060101

Title: Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of beta-ketoesters and unsaturated N-acylthiazolidinethiones.

Journal: Journal of the American Chemical Society 20050810

Title: Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones.

Journal: Journal of the American Chemical Society 20050803

Title: A study of [Co2(alkyne)(binap)(CO)4] complexes (BINAP=(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine)).

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20050408

Title: Enantioselective protonation of silyl enolates catalyzed by a BinapAgF complex.

Journal: Angewandte Chemie (International ed. in English) 20050225

Title: Enantioselective synthesis of six-membered palladacycles having metal-bound stereogenic carbons: isolation and reactivity of palladacycles containing readily accessible beta-hydrogens.

Journal: Journal of the American Chemical Society 20041229

Title: Stereospecific, enantioselective allylation of alpha-hydrazono esters by using allyltrichlorosilanes with BINAP dioxides as neutral-coordinate organocatalysts.

Journal: Angewandte Chemie (International ed. in English) 20041203

Title: Synthesis and coordinating ability of an anionic cobaltabisdicarbollide ligand geometrically analogous to BINAP.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20041025

Title: Preparation of an amphiphilic resin-supported BINAP ligand and its use for rhodium-catalyzed asymmetric 1,4-addition of phenylboronic acid in water.

Journal: Organic letters 20040916

Title: Enantioselective tandem O-nitroso Aldol/Michael reaction.

Journal: Journal of the American Chemical Society 20040519

Title: Enantioselective O- and N-nitroso aldol synthesis of tin enolates. Isolation of three BINAP-silver complexes and their role in regio- and enantioselectivity.

Journal: Journal of the American Chemical Society 20040505

Title: Use of chiral zwitterionic surfactants for enantiomeric resolutions by capillary electrophoresis.

Journal: Electrophoresis 20030801

Title: Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.

Journal: Journal of the American Chemical Society 20030423

Title: Construction of monomeric and polymeric porphyrin compartments by a Pd(II)-pyridine interaction and their chiral twisting by a BINAP ligand.

Journal: The Journal of organic chemistry 20030207

Title: How to turn the catalytic asymmetric hydroboration reaction of vinylarenes into a recyclable process.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030103

Title: Progress in arylpiperazine synthesis by the catalytic amination reaction.

Journal: Bioorganic & medicinal chemistry 20021201

Title: Mechanistic insights into the Pd(BINAP)-catalyzed amination of aryl bromides: kinetic studies under synthetically relevant conditions.

Journal: Journal of the American Chemical Society 20021127

Title: Synthesis, characterization, and reactivity of arylpalladium cyanoalkyl complexes: selection of catalysts for the alpha-arylation of nitriles.

Journal: Journal of the American Chemical Society 20020814

Title: Polymer-supported catalysts: enantioselective hydrogenation and hydrogen transfer reduction.

Journal: Bioorganic & medicinal chemistry letters 20020722

Title: Polymer-supported chiral catalysts with positive support effects.

Journal: Bioorganic & medicinal chemistry letters 20020722

Title: Highly enantioselective syntheses of functionalized alpha-methylene-gamma-butyrolactones via Rh(I)-catalyzed intramolecular Alder ene reaction: application to formal synthesis of (+)-pilocarpine.

Journal: Journal of the American Chemical Society 20020717

Title: Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Journal: Journal of the American Chemical Society 20020410

Title: Pd-catalyzed asymmetric hydrogenation of alpha-fluorinated iminoesters in fluorinated alcohol: a new and catalytic enantioselective synthesis of fluoro alpha-amino acid derivatives.

Journal: Organic letters 20010208

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SDS
Tags:76189-56-5 Molecular Formula|76189-56-5 MDL|76189-56-5 SMILES|76189-56-5 (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene