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
• Article Data: 29

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

Description

(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL, also known as (R)-BINAP, is a chiral ligand derived from binaphthyl, a central structure in various organic compounds. It is characterized by its colorless solid appearance and is known for its unique stereochemistry, which makes it a valuable compound in the field of asymmetric catalysis.

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 
• 142010-99-9 3'-Chloro-2,2'-bis-methoxymethoxy-3-phenylsulfanyl-[1,1']binaphthalenyl 
• 142011-00-5 3'-Bromo-2,2'-bis-methoxymethoxy-3-phenylsulfanyl-[1,1']binaphthalenyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 349149-07-1 (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde 
• 142010-85-3 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl 
• 142010-78-4 2,2'-Bis-methoxymethoxy-3-phenylsulfanyl-[1,1']binaphthalenyl 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 142010-88-6 (rac)-3,3’-diiodo-2,2’-di(methoxymethoxy)-1,1’-binaphthyl 
• 142010-77-3 (2,2'-Bis-methoxymethoxy-[1,1']binaphthalenyl-3-yl)-phenyl-methanol 
• 791616-60-9 rac-3,3'-bis(4-nitrophenyl)-[1,1'-binaphthalene]-2,2'-diol 
• 142010-72-8 3-Bromo-2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 141779-46-6 2,2’-dihydroxy-[1,1’-binaphthalene]-3,3’-dicarbaldehyde 

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.

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

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).