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

Packsize	Purity	Availability	Price	Discounted Price
100mg	97%	in stock	$6.00	$4.00
250mg	97%	in stock	$8.00	$6.00
1g	97%	in stock	$10.00	$7.00
5g	97%	in stock	$13.00	$9.00
10g	97%	in stock	$24.00	$17.00
25g	97%	in stock	$58.00	$41.00
100g	97%	in stock	$218.00	$153.00

Description

• Catalog Number: AI56087
• 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

Computed Properties

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

Upstream Synthesis Route

The (S)-(-)-2,2-Bis(Diphenylphosphino)-1,1-Binaphthalene is a chiral ligand commonly employed in asymmetric catalysis. Its unique structure enables it to interact with metal catalysts and promote enantioselective reactions in chemical synthesis. This ligand has found applications in various organic transformations, including asymmetric hydrogenation, C-C bond formation, and other reactions where stereochemical control is essential. (S)-(-)-2,2-Bis(Diphenylphosphino)-1,1-Binaphthalene plays a crucial role in enhancing the efficiency and selectivity of the catalytic processes, leading to the production of optically pure compounds with high yields. Its utility in asymmetric catalysis has made it a valuable tool for synthetic chemists seeking to access enantiomerically enriched molecules for pharmaceuticals, agrochemicals, and other fine chemicals.

Literature

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  Acta crystallographica. Section E, Structure reports online 20120701

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  Chemistry, an Asian journal 20110301

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

  Organic letters 20101217

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

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

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  Organic & biomolecular chemistry 20100628

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  Inorganic chemistry 20100503

• Origin of intense chiroptical effects in undecagold subnanometer particles.

  Journal of the American Chemical Society 20100203

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

  Physical chemistry chemical physics : PCCP 20091021

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

  Chemical & pharmaceutical bulletin 20091001

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

  The Journal of organic chemistry 20090904

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

  The Journal of organic chemistry 20090116

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  Journal of the American Chemical Society 20081105

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  Chemistry, an Asian journal 20081006

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

  Organic & biomolecular chemistry 20071107

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

  Journal of the American Chemical Society 20070822

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

  Journal of the American Chemical Society 20070606

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  Organic letters 20070329

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

  Journal of the American Chemical Society 20070117

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

  Journal of the American Chemical Society 20061025

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  Chirality 20060801

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  The journal of physical chemistry. B 20060622

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

  Journal of the American Chemical Society 20060322

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  Journal of the American Chemical Society 20060308

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  Organic letters 20060302

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

  Magnetic resonance in chemistry : MRC 20060101

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

  Journal of the American Chemical Society 20050810

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

  Journal of the American Chemical Society 20050803

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

  Chemistry (Weinheim an der Bergstrasse, Germany) 20050408

• Enantioselective protonation of silyl enolates catalyzed by a BinapAgF complex.

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

  Journal of the American Chemical Society 20041229

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

  Angewandte Chemie (International ed. in English) 20041203

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

  Chemistry (Weinheim an der Bergstrasse, Germany) 20041025

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

  Organic letters 20040916

• Enantioselective tandem O-nitroso Aldol/Michael reaction.

  Journal of the American Chemical Society 20040519

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

  Journal of the American Chemical Society 20040505

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

  Electrophoresis 20030801

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

  Journal of the American Chemical Society 20030423

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

  The Journal of organic chemistry 20030207

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

  Chemistry (Weinheim an der Bergstrasse, Germany) 20030103

• Progress in arylpiperazine synthesis by the catalytic amination reaction.

  Bioorganic & medicinal chemistry 20021201

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

  Journal of the American Chemical Society 20021127

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

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