18531-96-9

Usage

Uses

Used in Pharmaceutical Industry:
S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID is used as an intermediate for the preparation of optically active 1,1'-binaphthyl quaternary ammonium salts. These salts act as chiral phase-transfer catalysts, which are essential in the synthesis of enantiomerically pure pharmaceutical compounds. The use of chiral catalysts ensures that the desired enantiomer is selectively produced, leading to more effective and safer drugs.
Used in Chemical Industry:
In the chemical industry, S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID is utilized as a key building block for the synthesis of various chiral ligands and catalysts. These chiral catalysts are employed in a wide range of asymmetric reactions, such as hydrogenation, hydroformylation, and epoxidation, to produce enantiomerically enriched products. The use of chiral catalysts in these reactions helps to improve the efficiency and selectivity of the process, leading to higher yields and reduced waste.
Used in Research and Development:
S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID is also used as a research tool in the development of new chiral catalysts and ligands. Its unique binaphthyl core structure provides a versatile platform for the design and synthesis of novel chiral molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 76373-16-5 1-Bromo-naphthalene-2-carboxylic acid 1-methyl-heptyl ester 
• 76373-12-1 l-menthyl 1-bromo-2-naphthoate 
• 124-38-9 carbon dioxide 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 619-44-3 methyl 4-iodobenzoate 
• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 
• 138488-70-7 Methyl 1-chloro-2-naphthoate 
• 7553-56-2 iodine 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 86457-66-1 (S)-1,1'-binaphthalene-2,2'-dicarbonyl dichloride 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 129207-26-7 (R)-1,1'-Binaphthalene-2-carbonitrile-2'-carbonyl chloride 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 

Downstream Products

• 641-13-4 anthanthrone 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 246140-16-9 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid monoglycidyl ester 
• 950889-62-0 3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-dicarboxylic acid 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 3594-94-3 (S)-2,2'-Bis-1,1'-binaphthyl 
• 86457-66-1 (S)-1,1'-binaphthalene-2,2'-dicarbonyl dichloride 

Relevant academic research and scientific papers

Synthesis and resolution of axially chiral C2-symmetric 1,1'-binaphthyl-substituted tetramethylethylenediamines

The axially chiral TMEDA derivatives 1 and 2 in which tetramethylethylenediamine is substituted respectively by one and two 1,1'-binaphthyl units at their 2,2'-positions, are of interest as chiral catalysts. Experimental details of their preparation in enantiomerically pure form are given. Two different routes have been followed, involving alkylation of both N,N-dimethyl ethylenediamine and ethylenediamine by 2,2'-bis-(bromomethyl)-1,1'-binaphthyl either enantiomerically pure as prepared from resolved 1,1'-binaphthyl-2,2'-dicarboxylic acid or racemic, the resulting racemic diamines 1 and 2 being then resolved with dibenzoyl-tartaric acid.

Convenient Optical Resolution of Axially Chiral 1,1'-Binaphthyl-2,2'-dicarboxylic Acid

Axially chiral 1,1'-binaphthyl-2,2'-dicarboxylic acid was conveniently resolved through its brucine salts in satisfactory yields.The resolved diacids were confirmed to be optically pure from high-performance liquid chromatographic analyses of the dimethyl esters derived from them on an optically active poly(diphenyl-2-pyridylmethyl methacrylate) column.

Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution

Enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acids (R)-1 and (S)-1 have been synthesized through the lipase-catalyzed kinetic resolution of the racemic 2,2-bis(hydroxymethyl)-1,1'-binaphthyl (±)-2 and subsequent oxidation of the hydroxymethyl groups. (C) 2000 Elsevier Science Ltd.

Practical synthesis of axially chiral dicarboxylates via Pd-catalyzed external-CO-free carbonylation

We have developed a safe and practical synthetic method for preparing axially chiral diphenyl dicarboxylates using Pd- catalyzed external-CO-free carbonylation with phenyl formate as a CO surrogate. Optimized conditions consisted of axially chiral [1,1′-binaphthalene]-2,2′-diyl ditriflate and its congeners, each easily prepared from commercially available enantiomerically pure diols, Pd(OAc)2, 1,3-bis(diphenylphosphino)-propane, ethyldiisopropylamine, and no solvent. To demonstrate the potential utility of these products, this method was conducted on gram-scale and the phenyl ester products were converted to other useful compounds, and both processes were carried out without difficulty.

Concise synthesis of binaphthol-derived chiral dicarboxylic acids

Abstract 3,3'-Disubstituted 1,1'-binaphthyl-2,2'-dicarboxylic acids (1) were synthesized in three or four steps from commercially available BINOL via carbon dioxide fixation with organolithium to incorporate the carboxylic acid moieties, followed by either carboxylate-directed ortho-C-H arylation or Suzuki cross-coupling. This method provides easy access to various types of axiially chiral dicarboxylic acids, which should be useful for studies of chiral Br?nsted acid-catalyzed asymmetric reactions.

Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2, 2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor

Dilithiation of optically active 2,2′-dibromo-1,1 ′-binaphthyl 2 with t-BuLi followed by carboxylation of the resulting dilithio-intermediate 3 with CO2 gave optically active 1,1′-binaphthyl-2,2′-dicarboxylic acid 1, which was further transformed to its dicyano derivative 4. Both of these transformations were carried out in a one-pot operation and the products were obtained in excellent yields with no observable racemization.

Stereoconservative cyanation of [1,1′-binaphthalene]-2,2′-dielectrophiles. An alternative approach to homochiral C2-symmetric [ 1,1′-binaphthalene]-2,2′-dicarbonitrile and its transformations

The performed study on the cyanation of [1,1′-binaphthalene]-2,2′-diiodide and [1,1′-binaphthalene]-2,2′-diyl ditriflate showed reactions with zinc cyanide catalyzed by palladium phosphane complex in DMF to be the most effective procedures with almost com

Anomalous CD/UV exciton splitting of a binaphthyl derivative: The case of 2,2′-diiodo-1,1′-binaphthalene

The UV and CD spectra of (R)-(+)-2,2′-diiodo-1,1′-binaphthalene show an unexpectedly large value of the wavelength splitting between the two main bands, resulting from the exciton coupling of 1Bb transitions. An hypothesis is proposed on transition moments directions, making it possible to relate quantitatively the observed splitting to the orthogonal arrangement found in the solid state and calculated for the structure in solution.

Embedding an allylmetal dimer in a chiral cavity: The unprecedented stereoselectivity of a twofold Wittig [1,2]-rearrangement

After α,α'-dimetalation, both 2,2′-diallyloxy-1,1′-binaphthyl and 2,2′-di-2-methylallyloxy-1,1′-binaphthyl undergo the Wittig rearrangement with perfect diastereoselectivity. When racemic 1,1′-binaphthyl-2,2′-diol ("BINOL") is used as the starting material, it gives rise to a 1:1 mixture of antipodal stereoisomers, whereas enantiomerically pure (M)-2,2′-diallyloxy-1,1′-binaphthyl affords (M)-(S,S)-1,1-(1,1′-binaphthyl-2,2′-diyl)bis(2-propen-1-ol) as the sole product. The (M)-(S,S)/(P)-(R,R) mixture resulting from the rearrangement of racemic 2,2′-diallyloxy-1,1′-binaphthyl can be effectively subjected to a kinetic racemate resolution by applying the Sharpless-Katsuki asymmetric epoxidation. The single-sided Wittig rearrangement of 2-allyloxy-2′-propyloxy-1,1′-binaphthyl proceeds without any diastereoselectivity as this substrate can only be monometalated and hence is incapable of intramolecular aggregate formation which is instrumental for the observed stereoselectivity. Copyright

Convenient synthesis of 1,1'-binaphthyl-2,2'-dicarboxylic acid

Two syntheses of 1,1'-binaphthyl-2,2'-dicarboxylic acid (4) in good yields are presented via the oxidation of the 2'-methyl substituent of isopropyl 2'-methyl-1,1'-binaphthyl-2-carboxylate (8), which is readily obtainable by the reaction of 2-methyl-1-naphthyl Grignard reagent 7 with isopropyl 1-isopropoxy-2-naphthoate (6).