102490-05-1

Basic information

• Product Name: S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol
• Synonyms: S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol;3,3'-Diphenyl-1,1'-binaphthalene-2,2'-diol;(S)-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol, 99%e.e.;(R)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol;(S)-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol, 98% (99% ee);(S)-3,3'-diphenyl-BINOL
• CAS NO: 102490-05-1
• Molecular Formula: C₃₂H₂₂O₂
• Molecular Weight: 438.51588
• Mol File: 102490-05-1.mol

Chemical Properties

• Boiling Point: 574.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.251±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.23±0.50(Predicted)
• CAS DataBase Reference: S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol(102490-05-1)
• EPA Substance Registry System: S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol(102490-05-1)

Safety Data

• Hazardous Substances Data: 102490-05-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is used as a chiral ligand in asymmetric synthesis and catalysis for the development of pharmaceutical compounds. Its unique structure allows for the creation of enantiomerically pure compounds, which is crucial in the synthesis of chiral drugs with specific biological activities.
Used in Materials Industry:
S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is used as a chiral ligand in the synthesis of chiral materials with specific properties, such as optically active polymers and liquid crystals. Its ability to induce chirality in these materials makes it valuable in the development of advanced materials with unique optical, electronic, and mechanical properties.
Used in Asymmetric Catalysis:
S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is used as a chiral ligand in metal-catalyzed asymmetric reactions, enabling the selective formation of enantiomerically pure products. Its ability to form complexes with metal ions enhances the efficiency and selectivity of these reactions, making it an essential component in the development of enantioselective catalysts.
Used in Complex Formation with Metal Ions:
S-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol is used to form complexes with metal ions, which can enhance its applications in asymmetric catalysis. The formation of these complexes can improve the stability, solubility, and reactivity of BINOL, allowing for more efficient and selective catalysis in various chemical reactions.

Upstream product

• 108-90-7 chlorobenzene 
• 602-09-5 1,1'-bi-2-naphthol 
• 30889-48-6 3‐phenylnaphthalen‐2‐ol 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 212191-84-9 (±)?3,3'?diphenyl?2,2'?dimethoxy?1,1'?binaphthalene 
• 428874-67-3 (±)?3,3'?diphenyl?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 100-58-3 phenylmagnesium bromide 
• 68251-77-4 2‐bromo‐3‐methoxynaphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 135-19-3 β-naphthol 
• 75640-70-9 3,3'-diphenyl-1,1'-bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 75684-93-4 (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol 
• 75640-70-9 (S)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-binaphthyl 
• 874948-59-1 (S)-(-)-3,3’-bisphenyl-1,1’-bi-2-naphthyl phosphoric acid 
• 882992-52-1 (11bS)-2,6-diphenyl-N-((S)-1-phenylethyl)-N-((S)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine 
• 882992-52-1 (R,R)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine 

Relevant articles and documents

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

Macromolecular helicity induction and memory in a poly(biphenylylacetylene) bearing an ester group and its application to a chiral stationary phase for high-performance liquid chromatography

An optically inactive poly(biphenylylacetylene) bearing an ester group at the 4′-position of the pendants formed a preferred-handed helical conformation and biased axial chirality in the pendants through a noncovalent interaction with a chiral alcohol, both of which were retained (memorized) even after removal of the chiral alcohol. The chiral stationary phase for high-performance liquid chromatography, prepared by coating the polymer with macromolecular helicity memory on silica gel, showed good chiral recognition ability towards various racemates.

Chromatographic enantioseparation by poly(biphenylylacetylene) derivatives with memory of both axial chirality and macromolecular helicity

Novel poly(biphenylylacetylene) derivatives bearing two acetyloxy groups at the 2- and 2′-positions and an alkoxycarbonyl group at the 4′-position of the biphenyl pendants (poly-Ac's) were synthesized by the polymerization of the corresponding biphenylylacetylenes using a rhodium catalyst. The obtained stereoregular (cis-transoidal) poly-Ac's folded into a predominantly one-handed helical conformation accompanied by a preferred-handed axially twisted conformation of the biphenyl pendants through noncovalent interactions with a chiral alcohol and both the induced main-chain helicity and the pendant axial chirality were maintained, that is, memorized, after complete removal of the chiral alcohol. The stability of the helicity memory of the poly-Ac's in a solution was lower than that of the analogous poly(biphenylylacetylene)s bearing two methoxymethoxy groups at the 2- and 2′-positions of the biphenyl pendants (poly-MOM's). In the solid state, however, the helicity memory of the poly-Ac's was much more stable and showed a better chiral recognition ability toward several racemates than that of the previously reported poly-MOM when used as a chiral stationary phase for high-performance liquid chromatography. In particular, the poly-Ac-based CSP with a helicity memory efficiently separated racemic benzoin derivatives into enantiomers.

MnI2-catalyzed dimerization of 2-hydroxyanthracene

Dimerization of 2-hydroxyanthracene was investigated with 5mol% of various catalysts that are efficient catalysts for the dimerization of 2-naphthol. Catalysts such as Cu(OH)Cl TMEDA, [Mn(acac) 3], and [Mn(acac) 2] did not give satis

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

RETRACTED ARTICLE: Enantioselective organocatalytic hantzsch synthesis of polyhydroquinolines

The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst scr

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.].

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.

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.

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.