135029-77-5

Basic information

• Product Name: R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine
• Synonyms: R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine;(R)-N,N,N',N'-Tetramethyl-1,1'-binaphthyldiamine,99%e.e.
• CAS NO: 135029-77-5
• Molecular Formula: C₂₄H₂₄N₂
• Molecular Weight: 340.46076
• Mol File: 135029-77-5.mol

Chemical Properties

• Boiling Point: 511.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.138±0.06 g/cm3(Predicted)
• PKA: 5.00±0.40(Predicted)
• CAS DataBase Reference: R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine(CAS DataBase Reference)
• NIST Chemistry Reference: R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine(135029-77-5)
• EPA Substance Registry System: R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine(135029-77-5)

Safety Data

• Hazardous Substances Data: 135029-77-5(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used as a ligand for forming stable complexes with metal ions. Its strong Lewis base character and nucleophilic nature make it suitable for use in coordination chemistry.
Used in Organic Synthesis:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used as a reagent in organic synthesis, where its electron-rich and sterically demanding nature can be utilized for various reactions.
Used in Catalysis:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used as a catalyst in various reactions, including asymmetric hydrogenation, cross-coupling, and ring-opening polymerization. Its ability to form stable complexes with metal ions makes it a versatile catalyst for these applications.
Used in Pharmaceutical Industry:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used in the pharmaceutical industry for the development of new drugs and drug candidates. Its complexation with metals and its use in catalytic applications can contribute to the synthesis of pharmaceutical compounds.
Used in Agrochemical Industry:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used in the agrochemical industry for the development of new agrochemicals and pesticides. Its potential applications in coordination chemistry and catalysis can aid in the synthesis of agrochemical compounds.
Used in Material Science:
R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine is used in material science for the development of new materials with unique properties. Its electron-rich and sterically demanding nature can be utilized in the synthesis of advanced materials.

Upstream product

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

Relevant articles and documents

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.

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.

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.