3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane
[CAS# 35141-30-1]

Identification

• Classification: Chemical reagent >> Silane reagent
• Name: 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane
• Synonyms: 2-[2-(3-Trimethoxysilylpropylamino)ethylamino]ethylamine; (3-(Trimethoxysilyl)propyl)diethylenetriamine
• Molecular Formula: C₁₀H₂₇N₃O₃Si
• Molecular Weight: 265.43
• CAS Registry Number: 35141-30-1
• EC Number: 252-390-9
• SMILES: CO[Si](CCCNCCNCCN)(OC)OC

Properties

• Density: 1.031
• Boiling point: 114-118 °C (2 mmHg)
• Refractive index: 1.457-1.461
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302+H332-H302-H312-H314-H317-H318-H319-H332-H411
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P330-P333+P317-P337+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1A	H317
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1B	H317
Reproductive toxicity	Repr.	1B	H360FD
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1C	H314
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H336

• Transport Information: UN 2735

Discovery and Applications

3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane is an organosilicon compound that has garnered attention for its multifunctional applications, particularly in the fields of materials science, surface modification, and biomedicine. This compound, often referred to as a silane coupling agent, is characterized by the presence of amino groups and a trimethoxysilane functional group, which enables it to interact with both organic and inorganic materials. The discovery and development of this compound stem from the broader need for effective agents that can enhance adhesion, modify surfaces, and improve material properties.

The synthesis of 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane typically involves the reaction of aminoethylaminopropylsilane with trimethoxysilane. The resulting compound features a propyl chain linking a trimethoxysilane group to a branched amine structure, providing it with unique chemical properties that are beneficial for a variety of applications. The multifunctionality of this silane enables it to act as both a coupling agent and a surface modifier, enhancing the interfacial adhesion between organic polymers and inorganic materials.

One of the primary applications of 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane is in the field of polymer science, where it serves as a coupling agent in composite materials. By improving the bonding between the polymer matrix and inorganic fillers such as silica or alumina, this silane enhances the mechanical strength and durability of composite materials. This application is particularly significant in industries such as automotive, aerospace, and construction, where high-performance materials are required.

In addition to its use in composites, this silane compound has found applications in the formulation of adhesives and sealants. The presence of amino groups contributes to improved adhesion properties, enabling these materials to bond effectively to various substrates, including metals, glass, and ceramics. This enhances the overall performance of adhesives in applications such as construction, automotive assembly, and electronics.

Another area of interest for 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane is in biomedical applications. Due to its biocompatibility and ability to functionalize surfaces, this silane is being explored for use in drug delivery systems and tissue engineering. The amino groups can facilitate the attachment of biological molecules, promoting cell adhesion and growth on implantable materials. This characteristic is crucial for developing medical devices and scaffolds that can effectively integrate with biological tissues.

Furthermore, the compound has potential applications in the formulation of anti-corrosion coatings. The silane can form a protective layer on metal surfaces, preventing oxidation and corrosion, which is particularly important in marine and industrial environments. This protective feature enhances the longevity and performance of metal components, reducing maintenance costs and extending service life.

Safety considerations are paramount when handling 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane. While it is generally regarded as safe when used appropriately, precautions should be taken to minimize exposure, particularly to vapors and skin contact. Standard safety protocols and personal protective equipment are recommended to ensure safe handling in industrial and laboratory settings.

In conclusion, 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane is a versatile organosilicon compound with significant applications in materials science, adhesives, and biomedical engineering. Its ability to enhance adhesion and modify surfaces makes it a valuable tool in various industries, while ongoing research continues to explore its potential in innovative applications.

References

2022. Silane Coupling Agents in Material Science. Materials Today, 55.
DOI: 10.1016/j.mattod.2022.02.012