604-60-4

Basic information

• Product Name: 2,2'-binaphthyl-1,1'-diol
• Synonyms: 2,2'-binaphthyl-1,1'-diol;2,2'-Bi(1-naphthol);2,2'-Binaphthalene-1,1'-diol;2-(1-hydroxy-2-naphthyl)-1-naphthol;2-(1-hydroxynaphthalen-2-yl)naphthalen-1-ol
• CAS NO: 604-60-4
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.32396
• EINECS: 210-072-7
• Mol File: 604-60-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 212 °C
• Boiling Point: 486.9±30.0 °C(Predicted)
• Appearance: /
• Density: 1.302±0.06 g/cm3(Predicted)
• PKA: 8.42±0.50(Predicted)
• CAS DataBase Reference: 2,2'-binaphthyl-1,1'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-binaphthyl-1,1'-diol(604-60-4)
• EPA Substance Registry System: 2,2'-binaphthyl-1,1'-diol(604-60-4)

Safety Data

• Hazardous Substances Data: 604-60-4(Hazardous Substances Data)

Usage

General Description

2,2'-binaphthyl-1,1'-diol is a chemical compound that is often used as a chiral ligand in organic synthesis and catalysis. It is an important building block in asymmetric catalysis and is known for its ability to form stable and highly efficient chiral catalysts. The compound consists of two naphthalene rings connected by a central carbon with hydroxyl groups attached at the 1 and 1' positions. Its unique structure and steric arrangement make it a valuable tool in the synthesis of chiral molecules and drugs. Additionally, it has found applications in pharmaceuticals, agrochemicals, and material science, making it a versatile and important chemical in modern organic chemistry.

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 
• 805977-21-3 [2,2']binaphthyl-1,1'-disulfonic acid 
• 10034-85-2 hydrogen iodide 
• 4900-62-3 2-nitro-1-methoxynaphthalene 
• 3178-03-8 1-methoxynaphthalen-2-amine 
• 151560-43-9 2-Iodo-1-methoxynaphthalene 
• 2216-69-5 1-Methoxynaphthalene 
• 771-15-3 2-bromo-1-naphthol 
• 62012-54-8 2-bromo-1-methoxynaphthalene 
• 252670-79-4 (1-methoxynaphthalen-2-yl)boronic acid 
• 135-19-3 β-naphthol 

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 articles and documents

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.

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.