103459-11-6

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Binaphthalene]-2,2'-diaMine, N,N,N',N'-tetraMethylis used as a chiral ligand for the synthesis of various pharmaceuticals. Its application is crucial in asymmetric synthesis, enabling the production of enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Fine Chemicals Industry:
In the fine chemicals industry, [1,1'-Binaphthalene]-2,2'-diaMine, N,N,N',N'-tetraMethylis used as a chiral ligand for the synthesis of high-quality specialty chemicals. Its role in asymmetric synthesis ensures the production of enantiomerically pure compounds, which are vital for various applications, including fragrances, dyes, and agrochemicals.
Used in Catalyst Preparation:
[1,1'-Binaphthalene]-2,2'-diaMine, N,N,N',N'-tetraMethylis used as a component in the preparation of metal complexes that serve as catalysts for asymmetric organic transformations. These catalysts are essential for enhancing the selectivity and efficiency of chemical reactions, leading to the production of desired enantiomers with high purity.

Upstream product

• 50-00-0 formaldehyd 
• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 580-13-2 2-bromonaphthalene 
• 578-58-5 2-methylmethoxybenzene 
• 2436-85-3 2-N,N-Dimethylaminonaphthalene 
• 121-69-7 N,N-dimethyl-aniline 

Relevant academic research and scientific papers

Solution Conformation of Two C2-Symmetric Amino Derivatives of 1,1'-Binaphthalene by Circular Dichroism and Liquid Crystal Technique

The solution conformation of two C2-symmetric 1,1'-binaphthyl compounds (N,N,N',N'-tetramethyl--2,2'-diamine (1) and N,N'-dimethyl--2,2'-diamine (2)) has been studied by MMX calculations, analysis of the adsorption and CD spectra, and induction of cholesteric mesophases in nematic liquid crystals.All these methods indicate that 1 prefers a cisoid conformation and that 2 assumes a conformation where the two naphthyl moieties are quasi-perpendicular.

Heterogeneous Rhodium-Catalyzed Aerobic Oxidative Dehydrogenative Cross-Coupling: Nonsymmetrical Biaryl Amines

The first heterogeneously catalyzed oxidative dehydrogenative cross-coupling of aryl amines is reported herein. 2-Naphthylamine analogues were reacted with various electron-rich arenes using a heterogeneous Rh/C catalyst under mild aerobic conditions, thus affording nonsymmetrical biaryl amines in excellent yields with high selectivities. This reaction provides a mild, operationally simple, and efficient approach for the synthesis of biaryls which are important to pharmaceutical and materials chemistry. A jab-cross move: A heterogeneously catalyzed oxidative dehydrogenative cross-coupling of aryl amines is reported. Aryl amines were treated with various arenes using a heterogeneous Rh/C catalyst under mild aerobic conditions to selectively afford cross-coupled products, and provides an efficient synthetic method for the preparation of nonsymmetrical biaryl amines by oxidative C-H activation.

Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.