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
• Article Data: 4

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

General Description

R-N,N,N',N'-tetramethyl-1,1'-binaphthyldiamine, also known as tetrakis(dimethylamino) ethylene (TDAE), is a diamine compound with the chemical formula C32H34N2. It is a highly electron-rich and sterically demanding diamine which is used as a ligand in coordination chemistry and as a reagent in organic synthesis. TDAE acts as a strong Lewis base due to its highly nucleophilic nature, and it can form stable complexes with a variety of metal ions. Its complexation with metals has been explored in catalytic applications for various reactions, including asymmetric hydrogenation, cross-coupling, and ring-opening polymerization. TDAE is a versatile reagent with potential applications in the pharmaceutical, agrochemical, and material science industries.

Upstream product

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• 50-00-0 formaldehyd 
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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.

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.