N-[3-(Trimethoxysilyl)propyl]ethylenediamine
[CAS# 1760-24-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: N-[3-(Trimethoxysilyl)propyl]ethylenediamine
• Synonyms: [3-(2-Aminoethyl)aminopropyl]trimethoxysilane; DAMO
• Molecular Formula: C₈H₂₂N₂O₃Si
• Molecular Weight: 222.36
• CAS Registry Number: 1760-24-3
• EC Number: 217-164-6
• SMILES: CO[Si](CCCNCCN)(OC)OC

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 1.024 g/mL (4 °C)
• Index of Refraction: 1.441, Calc.^*, 1.4425-1.4445
• Boiling Point: 272.2±0.0 °C (760 mmHg), Calc.^*, 261-263 °C
• Flash Point: 108.1±21.8 °C, Calc.^*, 136 °C
• Water solubility: Reacts

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H302-H315-H317-H318-H332-H373-H412
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Respiratory sensitization	Resp. Sens.	1	H334
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H413
Eye irritation	Eye Irrit.	2	H318

Discovery and Applications

N-[3-(Trimethoxysilyl)propyl]ethylenediamine, often referred to as a silane coupling agent, is a chemical compound that has garnered significant attention in materials science and chemistry. It is characterized by its unique structure that combines an ethylenediamine moiety with a trimethoxysilyl group. This compound was developed in the late 20th century as researchers explored the potential of silane compounds in enhancing the bonding between organic materials and inorganic surfaces. The discovery of this silane derivative opened up new avenues for improving material properties and performance in various applications.

The synthesis of N-[3-(trimethoxysilyl)propyl]ethylenediamine typically involves the reaction of 3-(trimethoxysilyl)propyl chloride with ethylenediamine, resulting in the formation of the desired compound. This synthetic pathway underscores the versatility of silane chemistry and the ability to modify surface properties through chemical bonding. The trimethoxysilyl group allows for the formation of covalent bonds with silica and other inorganic materials, which enhances the adhesion and compatibility of different materials.

One of the primary applications of N-[3-(trimethoxysilyl)propyl]ethylenediamine is in the field of polymer composites. By incorporating this silane coupling agent into polymer matrices, manufacturers can improve the adhesion between the polymer and inorganic fillers, such as glass fibers or silica. This enhancement in adhesion leads to improved mechanical properties, such as increased tensile strength, impact resistance, and thermal stability. As a result, materials modified with this silane exhibit superior performance in applications ranging from automotive parts to construction materials.

In addition to its use in polymer composites, N-[3-(trimethoxysilyl)propyl]ethylenediamine plays a critical role in the formulation of coatings and adhesives. The presence of the trimethoxysilyl group promotes adhesion to various substrates, including metals, glass, and ceramics. This property makes it particularly useful in the manufacturing of protective coatings that require strong adhesion to surfaces exposed to harsh environments. Furthermore, the incorporation of this silane into adhesive formulations enhances bond strength, making it ideal for applications in industries such as electronics, aerospace, and automotive.

Moreover, N-[3-(trimethoxysilyl)propyl]ethylenediamine has shown promise in the field of surface modification. The silane can be used to functionalize surfaces, creating hydrophobic or hydrophilic characteristics depending on the application requirements. This capability is particularly beneficial in the development of self-cleaning surfaces and anti-fogging coatings. The ability to modify surface properties has significant implications in various sectors, including biomedical devices, where biocompatibility and surface characteristics are critical for device performance.

While N-[3-(trimethoxysilyl)propyl]ethylenediamine offers numerous advantages, it is essential to consider the safety and environmental implications associated with its use. Silanes can pose health risks if inhaled or if they come into contact with skin, necessitating proper safety precautions during handling and application. Additionally, the environmental impact of silane coupling agents is an area of ongoing research, prompting the need for sustainable practices in their use and disposal.

In summary, N-[3-(trimethoxysilyl)propyl]ethylenediamine is a valuable silane coupling agent that has transformed the fields of materials science and engineering. Its discovery has enabled significant advancements in the development of polymer composites, coatings, adhesives, and surface modification techniques. As research continues to explore its potential, this compound stands as a testament to the importance of chemical innovation in addressing the challenges of modern materials.

References

1982. The effect of methylene chain length on the chromatographic behaviour of aminobonded silicas in high-performance thin layer chromatography. Chromatographia, 15.
DOI: 10.1007/bf02258886

2024. Removal, mechanistic and kinetic studies of Cr(VI), Cd(II), and Pb(II) cations using Fe3O4 functionalized Schiff base chelating ligands. Environmental science and pollution research international, 31.
DOI: 10.1007/s11356-024-35443-8

1993. Dioxygen Oxidation by the Metal-Immobilized Catalyst Derived from Silica and Montmorillonite Modified by Silane Coupling Reagent. The Activation of Dioxygen and Homogeneous Catalytic Oxidation.
DOI: 10.1007/978-1-4615-3000-8_57