Core Advantages and Typical Applications of Tetramethylethylenediamine

English Name: N,N,N′,N′-Tetramethylethylenediamine (TMEDA)

CAS No.: 110-18-9

Chromatographic Purity: ≥99.0%

Molecular Weight: 116.2

Flash Point: 50 °F

Physical Form: Liquid

Refractive Index: n20/D 1.4179 (lit.)

Density: 0.775 g/mL at 20 °C (lit.)

Applications: Pharmaceutical intermediate

N,N,N′,N′Tetramethylethylenediamine  (TMEDA, CAS No.: 110-18-9) is a multifunctional organic ligand with a unique structure and superior performance. It is widely used in organic synthesis, metal complexation, lithium reagent reactions, catalytic systems, and various fine chemical and research fields. This article provides a comprehensive analysis of its core advantages and systematically summarizes its typical application scenarios in industry and research.

I. Molecular Structure and Physicochemical Properties of Tetramethylethylenediamine

Tetramethylethylenediamine is N,N,N',N'-tetramethylated ethylenediamine, with the structural formula (CH₃)₂NCH₂CH₂N(CH₃)₂. At room temperature, it is a colorless to pale yellow transparent liquid, with the following typical properties:

III. Detailed Typical Application Fields

Ligand in Organolithium Reaction Systems

TMEDA is widely used in reactions involving n-butyllithium (n-BuLi), tert-butyllithium (t-BuLi), and other organolithium reagents. By chelating lithium ions to form monomeric structures, it enhances the efficiency and selectivity of lithiation reactions, particularly in aromatic lithiation and α-carbon metalation reactions.

Stabilizer in Metal Catalytic Systems

In copper-catalyzed and palladium-catalyzed cross-coupling reactions (such as Ullmann reactions and Sonogashira couplings), TMEDA can act as a co-ligand to improve catalyst stability and increase reaction yields.

Complexation Extraction and Metal Separation

TMEDA has a strong complexation ability with heavy metal ions (such as Ni²⁺, Cu²⁺, Fe³⁺). It is used as a complexing agent or auxiliary extractant in hydrometallurgy, metal extraction, and ion-selective adsorption processes.

Additive for Batteries and Electrolytes

In lithium and magnesium battery research, TMEDA is used as an electrolyte complexing agent to regulate the dissolution behavior of metal ions, helping to improve battery performance and cycling stability.

Pharmaceutical Intermediate Synthesis

Due to its excellent Lewis base properties and its ability to promote base-sensitive reactions, TMEDA is often used in the synthesis of nitrogen-containing heterocycles, organosilicon compounds, and amine intermediates.

IV. Practical Application Examples

N,N,N′,N′Tetramethylethylenediamine  (TMEDA), with its outstanding diamine coordination structure, high reactivity, and good solubility, plays an irreplaceable role in modern organic chemistry and metal coordination chemistry. Whether in research laboratories or industrial synthesis, its applications as an auxiliary ligand, stabilizer, and complexing agent continue to expand. With the advancement of green synthesis and high-efficiency reaction systems, the market potential for TMEDA remains broad in the future.