N,N,N'-Trimethylethylenediamine
[CAS# 142-25-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: N,N,N'-Trimethylethylenediamine
• Molecular Formula: C₅H₁₄N₂
• Molecular Weight: 102.18
• CAS Registry Number: 142-25-6
• EC Number: 205-529-2
• SMILES: CNCCN(C)C

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*, 0.804 g/mL (Expl.)
• Boiling point: 117.0 °C 760 mmHg (Calc.)^*, 116 - 118 °C (Expl.)
• Flash point: 9.4 °C (Calc.)^*, 9 °C (Expl.)
• Index of refraction: 1.425 (Calc.)^*, 1.419 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H225-H314
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 2733

Discovery and Applications

N,N,N'-Trimethylethylenediamine (often abbreviated as TMEDA) is an organic compound that belongs to the class of ethylenediamine derivatives. It is a colorless liquid at room temperature and is primarily used as a ligand in coordination chemistry, specifically in the synthesis of metal complexes. TMEDA is known for its ability to form stable complexes with various metal ions, particularly transition metals, and is widely used in organic synthesis and catalysis.

The discovery of N,N,N'-Trimethylethylenediamine dates back to the early 20th century, as researchers sought to understand and improve the properties of ethylenediamine derivatives. It is a simple molecule that features two nitrogen atoms, each bound to a methyl group, connected by an ethylene backbone. Its chemical structure can be described as (CH₃)₂NCH₂CH₂N(CH₃)₂. The methyl groups on the nitrogen atoms make TMEDA a sterically bulky molecule, and this property plays a crucial role in its chemical behavior.

TMEDA is a versatile ligand in the field of coordination chemistry, where it is used to stabilize metal centers in various oxidation states. It has been employed in the synthesis of numerous metal complexes, particularly those involving lithium, magnesium, and other alkaline earth metals. The nitrogen atoms in TMEDA serve as electron-donating groups, forming coordination bonds with metal ions and stabilizing the metal center. This makes TMEDA an effective chelating agent in both organic and inorganic reactions.

One of the most important applications of N,N,N'-Trimethylethylenediamine is in organometallic chemistry. It is commonly used as a ligand in the preparation of complexes with transition metals, such as those used in catalytic processes. For example, TMEDA is frequently used in reactions involving alkyl and aryl metal compounds, where it helps to stabilize the metal species and facilitate various transformations, including cross-coupling reactions, polymerization, and other types of metal-mediated organic synthesis.

In addition to its role in metal complexation, TMEDA is also utilized as a base in certain reactions, particularly in organic synthesis. It can deprotonate weak acids and is employed in the preparation of organolithium reagents, which are widely used in synthetic chemistry. TMEDA is often used in combination with other bases or metal salts to facilitate reactions such as nucleophilic substitution, addition, and elimination.

Beyond its use in catalysis and organic synthesis, TMEDA has applications in the preparation of certain types of polymers and materials. For example, it can be involved in the synthesis of specialized ligands for materials science and the development of novel materials with specific properties.

Despite its usefulness in various chemical processes, TMEDA must be handled with care due to its potential to be toxic and its ability to react with strong oxidizers or acids. Safety precautions are necessary when working with TMEDA to avoid accidental exposure or chemical reactions that could pose risks.

The compound is also used in the preparation of certain pharmaceuticals, where it acts as a reagent in the synthesis of specific active pharmaceutical ingredients (APIs). It has also been explored in the production of certain specialty chemicals and in research applications that involve coordination chemistry or metal-based catalysis.

In conclusion, N,N,N'-Trimethylethylenediamine is an important chemical compound in coordination chemistry and organic synthesis, with a broad range of applications in catalysis, organometallic chemistry, and material science. Its ability to stabilize metal centers and facilitate chemical reactions makes it a valuable tool in the synthesis of metal complexes and the development of new chemical processes.

References

1982. Protonation Values for Other Ligands. Critical Stability Constants.
DOI: 10.1007/978-1-4615-6761-5_24