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
• Article Data: 93

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

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 
• 604-53-5 (R)-(+)-2,2'bis(diphenylphosphino)-1,1'-binaphthalene 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 132532-04-8 (R)-(+)-2-(diphenylphosphinyl)-2'-[(trifluoromethanesulfonyl)oxy]-1,1'-binaphthyl 
• 121457-42-9 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 
• 946863-69-0 (R)-(2-methoxyphenyl)(1-(naphthalen-8-yl)naphthalen-2-yl)phenylphosphine 
• 773881-95-1 (S)-2-(p-methoxybenzyl)-2'-methoxymethoxy-1,1'-binaphthyl 
• 773881-96-2 (S)-2'-(p-methoxybenzyl)-2-methoxymethoxy-3-hydroxybinaphthyl 

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.

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.

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