173831-50-0

Basic information

• Product Name: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL
• Synonyms: 2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(R)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1-BINAPHTHALENE;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(S)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL
• CAS NO: 173831-50-0
• Molecular Formula: C₂₄H₂₂O₄
• Molecular Weight: 374.43
• Product Categories: Other Ligands;Catalysis and Inorganic Chemistry;Chemical Synthesis;BINOLs;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;BINOL Series;Chiral Oxygen
• Mol File: 173831-50-0.mol

Chemical Properties

• Melting Point: 92-96 °C(lit.)
• Boiling Point: 477.809 °C at 760 mmHg
• Flash Point: 126.215 °C
• Appearance: white/Powder
• Density: 1.182 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(173831-50-0)
• EPA Substance Registry System: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(173831-50-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61-36/39-25
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 173831-50-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as an intermediate in the symmetric synthesis of BINOL-terpyridine ligands, which are essential in the development of novel catalysts for various chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a key component in the synthesis of 3or 3,3′-di-substituted products. These products can be obtained easily via ortho-metallation and subsequent treatment with an electrophile, leading to the formation of the corresponding BINOL derivatives. These derivatives are valuable in the development of new drugs and pharmaceutical compounds.
Used in Asymmetric Catalysis:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a chiral ligand in asymmetric catalysis, a field that focuses on the selective synthesis of enantiomerically pure compounds. Its unique stereochemistry allows for the creation of catalysts that can selectively produce one enantiomer over the other, which is crucial in the development of drugs with fewer side effects and improved efficacy.
Used in Research and Development:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is also used in research and development for the exploration of new synthetic routes and the development of novel catalysts. Its versatile structure and unique properties make it an attractive candidate for further investigation and application in various chemical processes.

Reaction

Starting material for the preparation of a variety of 3,3'-substituted binaphthols.

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 602-09-5 1,1'-bi-2-naphthol 
• 602-09-5 (R)-binaphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 150587-19-2 methoxymethoxy chloride 
• 135-19-3 β-naphthol 

Downstream Products

• 142010-84-2 2,2'-Bis-methoxymethoxy-3,3'-bis-triphenylsilanyl-[1,1']binaphthalenyl 
• 142010-77-3 (2,2'-Bis-methoxymethoxy-[1,1']binaphthalenyl-3-yl)-phenyl-methanol 
• 142010-88-6 (rac)-3,3’-diiodo-2,2’-di(methoxymethoxy)-1,1’-binaphthyl 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 142010-78-4 2,2'-Bis-methoxymethoxy-3-phenylsulfanyl-[1,1']binaphthalenyl 
• 142010-85-3 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl 
• 349149-07-1 (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde 
• 223389-51-3 2,2’-bis(methoxymethoxy)-[1,1’-binaphthalene]-3,3’-dicarbaldehyde 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 309269-73-6 3,3'-bis-(hydroxy-diphenyl-methyl)-[1,1']binaphthalenyl-2,2'-diol 
• 905569-19-9 3,3'-bis-(hydroxy-di-p-tolyl-methyl)-[1,1']binaphthalenyl-2,2'-diol 
• 905569-20-2 3,3'-bis-[bis-(2,5-dimethyl-phenyl)-hydroxy-methyl]-[1,1']binaphthalenyl-2,2'-diol 
• 905569-21-3 3,3'-bis-[hydroxy-bis-(2,3,5-trimethyl-phenyl)-methyl]-[1,1']binaphthalenyl-2,2'-diol 
• 75640-70-9 3,3'-diphenyl-1,1'-bi-2-naphthol 

Relevant articles and documents

Molecular recognition of aliphatic diamines by 3,3′- di(trifluoroacetyl)-1,1′-bi-2-naphthol

The fluorescent responses of 3,3′-di(trifluoroacetyl)-1,1′-bi- 2-naphthol toward a variety of amines have been studied. It was found that the aliphatic primary 1,2- and 1,5-diamines can greatly enhance the fluorescence of this compound, but under the same conditions, primary, secondary, and tertiary monoamines cannot turn on the fluorescence of this compound. In addition, this compound was shown to be an enantioselective and diastereoselective fluorescent sensor for chiral diamines. UV absorption and NMR spectroscopic methods have been used to study the interaction of the sensor with amines. These studies have demonstrated that the intramolecular OH···O=C hydrogen bonding of the sensor is important for both the reactivity of its trifluoroacetyl group with the amines and its fluorescent responses. The interaction of both of the two amine groups of a diamine molecule with the sensor is essential for the observed fluorescent sensitivity and selectivity.

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

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

1, 1'-bi-2-naphthol derivative and application thereof as fluorescent dye for aqueous coating

The invention relates to a 1, 1'-bi-2-naphthol derivative and an application thereof as fluorescent dye for aqueous coating, the 1, 1'-bi-2-naphthol derivative is a compound shown in a first formula.The 1, 1'-bi-2-naphthol derivative can be used as fluore

Strong Aggregation-Induced CPL Response Promoted by Chiral Emissive Nematic Liquid Crystals (N*-LCs)

In this paper we designed a kind of aggregation-induced emission (AIE) chiral fluorescence emitters (R/S-BINOL-CN enantiomers) in the aggregate state. Chiral emissive nematic liquid crystals (N*-LCs) prepared by doping this kind of AIE-active R/S-BINOL-CN enantiomers into a common achiral nematic liquid crystal (N-LC, E7) can self-assemble as the regularly planar Grandjean texture leading to high luminescence dissymmetry factor (glum) of aggregation-induced circularly polarized luminescence (AI-CPL) signal up to 0.41, which can be attributed to dipolar interactions from polar cyano groups and π–π interactions between binaphthyl moiety of the dopant R/S-BINOL-CN and biphenyl group of the host molecules (E7).

Aggregation-induced CPL response from chiral binaphthyl-based AIE-active polymers via supramolecular self-assembled helical nanowires

In this paper chiral polymer R-P could be synthesized by click polymerization reaction of (R)-3,3′-diethynyl-2,2′-bis(octyloxy)-1,1′-binaphthalene (R-M-1) and 1,2-bis(4-azidophenyl)-1,2-diphenylethene (M-2), and S-P was obtained by click polymerization re

The amplified circularly polarized luminescence emission response of chiral 1,1′-binaphthol-based polymers via Zn(II)-coordination fluorescence enhancement

Two kinds of chiral 1,1′-binaphthol (BINOL)-based polymer enantiomers were designed and synthesized by the polymerization of 5,5′-((2,2′-bis (octyloxy)-[1,1′-binaphthalene]-3,3′-diyl)bis(ethyne-2,1-diyl))bis(2-hydroxybenzaldehyde) (M1) with alkyl diamine (M2) via nucleophilic addition–elimination reaction. The resulting chiral polymers can exhibit mirror image cotton effects either in the absence or in the presence of Zn2+ ion. Almost no fluorescence or circularly polarized luminescence (CPL) emission could be observed for two chiral BINOL-based polymer enantiomers in the absence of Zn2+. Interestingly, the chiral polymers can show strong fluorescence and CPL response signals upon the addition of Zn2+, which can be attributed to Zn2+-coordination fluorescence enhancement effect. This work can develop a new strategy on the design of the novel CPL materials via metal-coordination reaction.

BINOL derivatives with aggression-induced emission

As fluorescent probes, the small Stokes shift and ACQ effect limit the application of BINOL derivatives. Herein, a new series of BINOL derivatives were synthesized which could be turned from ACQ to AIE fluorophores by changing the electron withdrawing group. Among these compounds, BIN-COP exhibits an obvious AIE property with low cytotoxicity. The bioimaging performance indicated that the designed fluorophores could be successfully used for bioimaging.

ESIPT-based ratiometric probe for Zn2+ detection based on BINOL framework

A ratiometric BINOL-based fluorescent probe for Zn2+ detection was rationally designed and synthesized. Based on the excited-state intramolecular proton transfer (ESIPT) mechanisms, the probe exhibited a significant variation on emission wavele

Compound boranil based on bi bisnaphthol of the framework and its preparation and use

The invention provides a series of Boranil compounds based on 1,1'-binaphthol parents, a preparation method of the compounds, and application of the compounds on detection of fluorine ions. The compounds meet one of the following general formulas, X is on