75684-93-4

Usage

Uses

Used in Pharmaceutical Industry:
R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is used as a chiral catalyst for the production of pharmaceuticals, leveraging its ability to control the stereochemistry of reactions. This ensures the synthesis of enantiomerically pure compounds, which is critical for the efficacy and safety of many drugs.
Used in Agrochemical Industry:
In the agrochemical sector, R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol serves as a chiral ligand in the synthesis of agrochemicals, contributing to the development of more effective and selective pesticides and other agricultural products.
Used in Fine Chemicals Production:
BINOL is utilized as a catalyst in the production of fine chemicals, where its chiral nature is essential for the creation of high-purity compounds used in various specialized applications.
Used in Synthesis of Complex Natural Products:
R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is employed as a key component in the synthesis of complex natural products, which are often the basis for new drug discoveries and have potential applications in materials science.
Used in Materials Science:
BINOL is used as a chiral tool in materials science, where its properties can influence the development of new materials with specific optical, electronic, or structural characteristics.

Upstream product

• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 428874-67-3 (±)?3,3'?diphenyl?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 108-90-7 chlorobenzene 
• 602-09-5 1,1'-bi-2-naphthol 
• 30889-48-6 3‐phenylnaphthalen‐2‐ol 
• 30478-88-7 3-bromo-2-naphthol 
• 98-80-6 phenylboronic acid 
• 75714-59-9 (Ra)-3,3’-dibromo-2,2’-dimethoxy-1,1’-binaphthalene 
• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 100-58-3 phenylmagnesium bromide 
• 135-19-3 β-naphthol 
• 93-04-9 2-Methoxynaphthalene 

Downstream Products

• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 
• 1427525-86-7 2,2'-bis(allyloxy)-3,3'-diphenyl-1,1'-binaphthyl 
• 75640-70-9 (S)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-binaphthyl 
• 874948-59-1 (R_a)-4-hydroxy-2,6-diphenyldinaphtho[1,3,2]dioxaphosphepine 4-oxide 
• 882992-52-1 C₄₈H₃₈NO₂P 

Relevant academic research and scientific papers

Photoinduced pitch changes in chiral nematic liquid crystals formed by doping with chiral diarylethene

Chiral binaphthyl derivatives having two photochromic diarylethene units were synthesized in an attempt to use them as dopants for photoresponsive liquid crystals. These compounds showed thermally irreversible photochromic reactions. The circular dichrois

Hypercrosslinking chiral Br?nsted acids into porous organic polymers for efficient heterogeneous asymmetric organosynthesis

Here, we developed a construction strategy for directly immobilizing the axially chiral phosphoric acid into hypercrosslinked polymers by a one-pot Friedel-Crafts alkylation reaction. The obtained chiral polymers have high porosity, excellent stability and tailorable catalytic centers, and display excellent activity, enantioselectivity and recyclability for asymmetric transfer hydrogenation.

Synthesis of (±)-3,3′-diphenyl-2,2′-binaphthol via different routes using Pd and Ni as catalyst respectively

3,3′-Biphenyl-2,2′-binaphthols (BINOLs) are precursors of phosphoric acids that are widely used as ligands and catalysts in organic reactions. In this report, two routes for the synthesis of (±)-3,3′-diphenyl BINOLs via (±)-3,3′ bis-halogenated BINOLs int

Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

Privileged biaryl frameworks, BINOL and NOBIN, were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions. The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities. This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency. Notably, the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions, providing an effective handle for further enriching the library of BINOLs and NOBINs. Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis. [Figure not available: see fulltext.].

Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols

An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

Design and synthesis of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a chiral fluorobissulfonyl scaffold

The first example of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from

INHIBITORS OF GLUCOSE TRANSPORTERS (GLUTS)

The present invention relates to 2,6-methanobenzo[g][1]oxacin-4-onecompounds and their analog compounds and pharmaceutically acceptable salts thereof as selective inhibitor of glucose transporters 1 and 3 (GLUTs 1 and 3), to methods of preparing said compounds, and to the use thereof as pharmaceutically active agents, especially for the prophylaxis and/or treatment of metabolic diseases, immunological diseases, autoimmune diseases, inflammation, graft versus host disease, cancer, and metastasis thereof. Furthermore, the present invention is directed to pharmaceutical composition comprising at least one of 2,6-methanobenzo[g][1]oxacin-4-one compounds and their analog compounds.

Double-Fold Ortho and Remote C-H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL

A double-fold ortho and remote C-H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C-H activation processes, respectively. While B2eg2 (eg = ethylene glyco

The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.

First enantioselective total synthesis of altersolanol A

The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric Diels-Alder (D-A) cycloaddition promoted by (R)-3,3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).