128544-05-8

Basic information

• Product Name: (S)-(+)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)
• Synonyms: BINOL-TF2;1,1'-BIS(2-NAPHTHOL) DITRIFLATE;1,1'-BINAPHTHYL-2,2'-DIYL BIS(TRIFLUOROMETHANESULPHONATE);1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE);1,1-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE);1,1'-BI-2-NAPHTHOL-BIS(TRIFLUOROMETHANESULPHONATE);(R)-TRIFLUOROMETHANESULFONIC ACID 2'-TRIFLUOROMETHANSULFONYLOXY-[1,1']BINAPHTHALENYL-2-YL ESTER;(RS)-TRIFLUOROMETHANESULFONIC ACID 2'-TRIFLUOROMETHANESULFONYLOXY-[1,1']BINAPTHALENYL-2-YL ESTER
• CAS NO: 128544-05-8
• Molecular Formula: C₂₂H₁₂F₆O₆S₂
• Molecular Weight: 588.49
• Product Categories: API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;BINOL Series;Chiral Oxygen
• Mol File: 128544-05-8.mol

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 578.8 °C at 760 mmHg
• Flash Point: 303.9 °C
• Appearance: white/Powder
• Density: 1.5402 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble
• Sensitive: moisture sensitive
• CAS DataBase Reference: (S)-(+)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(128544-05-8)
• EPA Substance Registry System: (S)-(+)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(128544-05-8)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 128544-05-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow powder

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 602-09-5 1,1'-bi-2-naphthol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 108-48-5 2,6-dimethylpyridine 
• 1025373-45-8 trifluoromethanesulfonic acid anhydride 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 

Downstream Products

• 85464-88-6 [1,1']binaphthyl-2,2'-dicarboxylic acid dimethyl ester 
• 618855-03-1 methyl 2'-hydroxy-<1,1'-binaphthyl>-2-carboxylate 
• 126613-07-8 (R)-1,1'-binaphthalene-2-methyl carboxylate-2'-trifluoromethane sulfonate 
• 610283-61-9 (S)-2-(bis(p-methoxyphenyl)phosphinyl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 
• 132532-07-1 [1,1'-binaphthalen]-2-yldiphenylphosphine oxide 
• 132532-04-8 (R)-(+)-2-(diphenylphosphinyl)-2'-[(trifluoromethanesulfonyl)oxy]-1,1'-binaphthyl 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 604-53-5 (R)-(+)-2,2'bis(diphenylphosphino)-1,1'-binaphthalene 
• 132548-91-5 (S)-(+)-2-hydroxy-2'-diphenylphosphinoyl-1,1'-binaphthyl 
• 132532-04-8 (R)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthalene 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 19634-89-0 (R)-2,2'-dimethyl-1,1'-binaphthyl 

Relevant articles and documents

Application of a Ferrocene-Based Palladacycle Precatalyst to Enantioselective Aryl-Aryl Kumada Coupling

The palladium catalysed reaction of 1-iodo-2-methylnaphthalene and 2-methyl-1-naphthylmagnesium bromide gave quantitatively an (Sa)-configured cross-coupled product in 80 % e.e. using (R,Sp)-PPFA as a ligand. N,N-Dimethylaminomethylferrocene was cyclopalladated (Na2PdCl4, (S)?Ac?Phe?OH, 93 % e.e., as determined by 1H NMR as a result of self-induced non-equivalence), and the resulting (Sp)-configured dimeric palladacycle was employed as a precatalyst for this cross-coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base-promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an (Sp)-configured product in up to 71 % e.e.

New bifunctional bis(Azairidacycle) with axial chirality via double cyclometalation of 2,2′-bis(aminomethyl)-1,1’-binaphthyl

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C-N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5-C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 ?C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C-H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.

The Trityl Cation Embedded into a [7]Helicene-Like Backbone: Preparation and Application as a Lewis Acid Catalyst

The synthesis of a helically chiral carbenium ion is reported. The new motif is essentially a trityl cation embedded into a [7]helicene-like framework. The key step in its preparation establishes the π-extended fluorenone system in one step by an unprecedented palladium-catalyzed carbonylative annulation of a 4,4′-biphenanthryl-3,3′-diyl precursor. The racemic form of the new carbon Lewis acid was found to catalyze a representative set of reactions typically promoted by the trityl cation.

Trost ligand with axial chiral binaphthyl skeleton and preparation method thereof

The invention discloses a novel optically pure binaphthyl Trost ligand and a preparation method thereof. (S)-2'-(diarylphosphine)-[1, 1'-binaphthyl]-2-carboxylic acid and chiral diamine are subjectedto condensation reaction to obtain the Trost ligand with

In Situ Generation of Ruthenium Carbonyl Phosphine Complexes as a Versatile Method for the Development of Enantioselective C?O Bond Arylation

We report here a method for in situ generation of various ruthenium carbonyl phosphine catalysts for arylation via cleavage of inert aromatic carbon–oxygen bonds. The use of catalyst systems consisting of [RuCl2(CO)(p-cymene)], CsF, styrene, an

Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands

The ability of alkali metal complexes featuring functionalized BINOL-derived ligands to catalyze ketone hydroboration reactions was explored. The reduced products were formed in excellent yields and with variable enantioselectivities dependent upon the nature of the ligand and the alkali metal cation.

Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

Axially Chiral, Electrophilic Fluorophosphonium Cations: Synthesis, Lewis Acidity, and Reactivity in the Hydrosilylation of Ketones

Axially chiral [(C6F5)3PF][B(C6F5)4] analogues based on dihydrophosphepines with a binaphthyl backbone were prepared and structurally characterized by X-ray diffraction analysis. Computational calculations of FIA and GEI values attest that these new fluorophosphonium cations have a higher Lewis acidity compared to the ubiquitous B(C6F5)3. Furthermore, application of these highly electrophilic compounds in the catalytic hydrosilylation of ketones and an investigation of the mechanism lead to a refined picture of the role of highly electrophilic fluorophosphonium cations.

Large Scale Synthesis of Chiral (3 Z,5 Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids

An advanced process for large scale (500 g) preparation of a (3Z,5Z)-2,7-dihydro-1H-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asymmetric synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II

Single-component, low molecular weight organic supergelators based on chiral barbiturate scaffolds

We report here the first chiral barbiturate to act as a single-component LMOG capable of gelating a variety of chlorinated and aromatic solvents. Solution-based DOSY NMR experiments, solid-state VP-SEM, and X-ray crystallography techniques were used to ch