128575-34-8

Basic information

• Product Name: (R)-(-)-1,1'-BI-2-NAPHTHOL 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(TRIFLUOROMETHANESULPHONATE);1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE);1,1-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE);(R)-TRIFLUOROMETHANESULFONIC ACID 2'-TRIFLUOROMETHANSULFONYLOXY-[1,1']BINAPHTHALENYL-2-YL ESTER;(RS)-TRIFLUOROMETHANESULFONIC ACID 2'-TRIFLUOROMETHANESULFONYLOXY-[1,1']BINAPTHALENYL-2-YL ESTER
• CAS NO: 128575-34-8
• Molecular Formula: C₂₂H₁₂F₆O₆S₂
• Molecular Weight: 550.45
• Product Categories: Organic Building Blocks;Organic Triflates;Sulfur Compounds
• Mol File: 128575-34-8.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: /
• Density: 1.591g/cm³
• CAS DataBase Reference: (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE)(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE)(128575-34-8)
• EPA Substance Registry System: (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE)(128575-34-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 128575-34-8(Hazardous Substances Data)

Usage

General Description

(R)-(-)-1,1'-Bi-2-naphthol bis(trifluoromethanesulfonate) is a compound that consists of two units of (R)-(-)-1,1'-bi-2-naphthol molecules linked by a bis(trifluoromethanesulfonate) group. It is a chiral and highly efficient catalyst that is commonly used in asymmetric synthesis and organic reactions. (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE) has been widely utilized in the preparation of various enantioenriched compounds and has demonstrated high stereoselectivity in many reactions. Its ability to catalyze a wide range of reactions, including Michael addition, Aldol reaction, and oxidation, makes it a valuable tool in chemical synthesis and research. Additionally, its relatively low toxicity and ease of handling have contributed to its popularity in the field of organic chemistry.

Upstream product

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

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 
• 132532-07-1 [1,1'-binaphthalen]-2-yldiphenylphosphine oxide 
• 132532-04-8 (R)-(+)-2-(diphenylphosphinyl)-2'-[(trifluoromethanesulfonyl)oxy]-1,1'-binaphthyl 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 132548-91-5 ((R)-2'-hydroxy-[1,1'-binaphthalen]-2-yl)diphenylphosphine oxide 
• 126613-06-7 (S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 

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.

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.