604-60-4

Usage

Uses

Used in Pharmaceutical Industry:
2,2'-binaphthyl-1,1'-diol is utilized as a chiral ligand for the synthesis of chiral molecules and drugs. Its unique structure and steric arrangement facilitate the creation of stable and highly efficient chiral catalysts, which are essential in the development of pharmaceuticals with specific biological activities.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2'-binaphthyl-1,1'-diol is employed as a chiral ligand for the synthesis of chiral agrochemicals. 2,2'-binaphthyl-1,1'-diol's ability to form stable and efficient chiral catalysts aids in the production of agrochemicals with targeted effects, reducing potential environmental impacts.
Used in Material Science:
2,2'-binaphthyl-1,1'-diol is also used as a chiral ligand in material science. Its unique structure and steric arrangement contribute to the development of advanced materials with specific properties, such as chiral polymers and other materials with potential applications in various industries.
Overall, 2,2'-binaphthyl-1,1'-diol is a versatile and significant chemical in modern organic chemistry, with applications spanning across pharmaceuticals, agrochemicals, and material science due to its role as a chiral ligand and its ability to form stable and efficient chiral catalysts.

Upstream product

• 90-15-3 α-naphthol 
• 113454-33-4 1,1’-dimethoxy-2-2’-binaphthalene 
• 7732-18-5 water 
• 7705-08-0 iron(III) chloride 
• 10034-85-2 hydrogen iodide 
• 135-19-3 β-naphthol 
• 252670-79-4 (1-methoxynaphthalen-2-yl)boronic acid 
• 62012-54-8 2-bromo-1-methoxynaphthalene 
• 771-15-3 2-bromo-1-naphthol 
• 2216-69-5 1-Methoxynaphthalene 
• 151560-43-9 2-Iodo-1-methoxynaphthalene 
• 3178-03-8 1-methoxynaphthalen-2-amine 
• 4900-62-3 2-nitro-1-methoxynaphthalene 
• 805977-21-3 [2,2']binaphthyl-1,1'-disulfonic acid 

Downstream Products

• 256382-41-9 6-{(1E)(3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one 
• 134169-13-4 (-)-(1S)-1-hydroxy-1-<3-(methylsulfonyl)-4-n-propoxy-5-(benzyloxy)phenyl>-4-(3,4,5-trimethoxyphenyl)butan-4-one 

Relevant academic research and scientific papers

Method for preparing electronic 2,2'-binaphthol

The invention discloses a method for preparing electronic 2,2'-binaphthol. The method comprises the following steps: under the action of a phase transfer catalyst and/or a surfactant, enabling 2-naphthol to react with a ferric trichloride solution and hydrogen peroxide, and finally performing reaction treatment with a water insoluble organic solvent, thereby obtaining an electron-grade product, namely 2,2'-binaphthol. Compared with the prior art, the method has the advantages that (1) the method has the advantages of a small amount of wastes of a solid-phase method and reaction balance, easiness in operation and low equipment requirements of a liquid-phase method; (2) the reaction efficiency is high, and a small amount of ferric chloride is used; (3) a product yield is high, and the highest product yield is up to 95%; (4) the product purity is improved, and electron-grade high requirements of electronic chemicals on raw materials are met; (5) a good production environment can be made,the working intensity is low, a small amount of wastewater is generated, and wastewater with ferrous ions can be oxidized and recycled.

Computational and DNMR investigation of the isomerism and stereodynamics of the 2,2′-binaphthalene-1,1′-diol scaffold

The relative stabilities of three conformational isomers of 2,2′-binaphthalene-1,1′-diol diisobutyrate and the energy barriers to rotation about the pivotal aryl-aryl bond and the two aryl-oxygen bonds were investigated by variable-temperature NMR spectroscopy in conjunction with DFT computations. The experimental and calculated data were found to be in very good agreement and provide new insights into the dynamic stereochemistry of BINOL-derived tropos ligands.

Chirality sensing of amines, diamines, amino acids, amino alcohols, and α-hydroxy acids with a single probe

A stereodynamic probe for determination of the absolute configuration and enantiomeric composition of chiral amines, diamines, amino alcohols, amino acids, and α-hydroxy carboxylic acids is described. The chirality sensing is based on spontaneous asymmetric transformation of the first kind with stereolabile binaphtholate boron and zinc complexes. The substrate binding and chiral amplification processes yield a distinctive chiroptical sensor output at high wavelength that can be used for rapid and accurate ee detection of minute sample amounts.

Bile acid derived tropos vaulted binaphthylphosphites: Synthesis, stereochemical characterization and complexation to rhodium

Three different 2,2'-binaphthylphosphites were synthesized, starting from suitable derivatives of cholic or deoxycholic acids and 1,1'-dihydroxy-2,2'- binaphthyl, and their stereochemical features were analyzed by CD and NMR spectroscopy. The spectroscopic data clearly demonstrate the capability of the cholestanic backbone to induce a M prevalent screw sense to the flexible binaphthyl moiety, giving rise to tropos ligands. The extent of the prevalence of the M sense of twist depends on the position at which the binaphthylphosphite moiety is linked on the bile acid skeleton. The three phosphites were mixed with [Rh(COD)2][BF4] and the resulting complexes were analyzed by variable temperature 31P NMR spectroscopy, thereby obtaining information on their stereochemical characteristics, which reflect the different asymmetric induction capability of the ligands. Copyright

SnCl4-mediated oxidative biaryl coupling reaction of 1-naphthol and subsequent ring closure of 2,2′-binaphthol to the dinaphthofuran framework

A simple method for the direct synthesis of 2,2′-binaphthols 2 and dinaphtho[1,2-b;2′,1′-d]furans 3 under mild conditions was developed, utilizing a biaryl coupling reaction via electron donor-acceptor complexes of 1-naphthols with SnCl4. Heating of the complex in a sealed tube for (18-24 h) afforded the corresponding o-o coupled product 2 in excellent yield. Prolonged reaction (56-65 h) under the same conditions afforded 3 in high yield in one step. We also found that in the case of α-naphthol without substituents other than a hydroxyl group at the C-1 position, regioselective o-o coupling reaction proceeded. The products 2a, 2b and 2g should be useful as synthetic intermediates for naturally occurring 3,3′-bijuglone, 3,3′-biplumbagin and elliptinone.

Tartaric acid amide derivative and method of producing the same

A d- or l-tartaric acid amide derivative serving as a host compound and a method of producing the amide derivative which combines with a guest compound to form a clathrate compound and which is expressed by the following Formula (A) or (B): STR1

Electrocatalytic Oxidative Coupling Reaction of Naphthols and Naphthol Ethers on a TEMPO Modified Graphite Felt Electrode

2-Naphthol and 2-methoxynaphthalene were quantitatively oxidized to the corresponding 1,1'-binaphthyls in more than 90percent current efficiency on a graphite felt electrode coated with a thin poly(acrylic acid) layer immobilizing 4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (4-amino-TEMPO). 1-Naphthol and 1-methoxynaphthalene were also completely converted to the predicted 1,1'-, 1,2'-, and 2,2'- positioned coupling products.The reaction proceeds via electrocatalytic oxidation of the modified-TEMPO species.The electrode was not inactivated during electrolysis and could be used repeatedly.

Prostanoids and synthesis thereof

Prostaglandin analogues which include a bicyclic isoxazolidine nucleus are disclosed. These analogues may be used to prepare other prostaglandins. Essential to the synthesis is intramolecular nitrone-alkene cycloaddition involving an alkenyl nitrone in which the reacting centers are separated by two carbons.

Thermolysis of Model Compounds for Coal. 2. Condensation and Hydrogen Transfer during Thermolysis of Naphthols

The dominant initial products from thermolysis of 1-naphthol in the liquid phase at 400 deg C are 2,2'-binaphthalene-1,1'-diol (2) and 1-tetralone (6).As reaction proceeds, binaphthol 2 undergoes rapid cyclization to dinaphthofuran (1), while ketone 6 is more slowly converted ultimately to naphthalene (8).The initial rate of this ring coupling and hydrogen-transfer reaction shows an apparent kinetic order of ca 2.5 in m-terphenyl diluent.In benzophenone solvent, formation of coupled binaphthol 2 is accelerated, but reduced product 6 is replaced by diphenylmethane.Thermolysis of 2-naphthol behaves similarly except that coupling occurs both between C-1 and C-1' to give dinaphthofuran (3), preceded by 1,1'-binaphthalene-2,2'-diol (4), and between C-1 and C-3' to give dinaphtho(2,1-b:2',3'-d>furan (5).The major reduction product is 2-tetralone (14).The ratio of (3 + 4)/5 decreases with increasing reaction time.Mechanistic hypotheses for this characteristic thermal behavior of phenols are explored.The significance of the reactions involved for conversion processes for coal, which contains significant phenolic functionality, is discussed.