N-Methylaminopropyltrimethoxysilane
[CAS# 3069-25-8]

Identification

• Classification: Chemical reagent >> Silane reagent
• Name: N-Methylaminopropyltrimethoxysilane
• Synonyms: Trimethoxy[3-(methylamino)propyl]silane; (3-Methylaminopropyl)trimethoxysilane; N-Methyl-3-aminopropyltrimethoxysilane
• Molecular Formula: C₇H₁₉NO₃Si
• Molecular Weight: 193.32
• CAS Registry Number: 3069-25-8
• EC Number: 221-334-5
• SMILES: CNCCC[Si](OC)(OC)OC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.978 g/mL (Expl.)
• Index of Refraction: 1.415, Calc.^*, 1.419 (Expl.)
• Boiling Point: 181.9±23.0 °C (760 mmHg), Calc.^*, 221.6 °C (Expl.)
• Flash Point: 63.8±22.6 °C, Calc.^*, 82 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

N-Methylaminopropyltrimethoxysilane is an organosilicon compound widely used in various industrial and chemical applications. The compound has the chemical formula C7H19NO3Si and consists of a trimethoxysilane group attached to a propyl chain that is further substituted with a methylamine group. This structure provides the compound with both silane functionality, making it useful in surface modification, and amine reactivity, enabling it to participate in a variety of chemical reactions.

The compound was first synthesized as part of research into silane coupling agents, which are used to improve the bonding between inorganic surfaces, such as glass or metal, and organic materials. Silane compounds, such as N-methylaminopropyltrimethoxysilane, are integral to enhancing the performance of composite materials, coatings, and adhesives by promoting stronger adhesion to substrates. The trimethoxysilane group in this compound allows it to bond effectively with the surfaces of materials, while the amine group can participate in further chemical reactions or enhance the interaction with other molecules.

N-Methylaminopropyltrimethoxysilane is primarily utilized as a coupling agent in the production of adhesives, coatings, and sealants. Its ability to improve the adhesion of these materials to substrates, especially in applications involving metals, ceramics, and glass, makes it valuable in industries such as automotive, construction, and electronics. Additionally, its presence in formulations for paints and coatings can improve the durability and resistance of these materials to environmental stressors.

In the field of materials science, N-methylaminopropyltrimethoxysilane is used in the preparation of functionalized surfaces. The amine group can be used to modify the surface properties of materials, such as enhancing their reactivity, wettability, or compatibility with other compounds. This is particularly useful in the development of advanced composite materials, where the surface chemistry of the components can significantly affect the overall performance of the final product.

Beyond surface modification, N-methylaminopropyltrimethoxysilane is also employed in the synthesis of organic-inorganic hybrid materials. Its ability to form silane bonds with inorganic materials while still retaining the functional reactivity of the amine group makes it suitable for creating composite materials with enhanced mechanical and thermal properties. These materials are used in a range of applications, including the production of coatings, films, and membranes.

The compound also plays a role in the production of silane-based polymers. Due to its chemical structure, N-methylaminopropyltrimethoxysilane can be incorporated into polymeric matrices, where it acts as a crosslinking agent or as a functional group that enables further chemical modifications. This versatility makes it useful in the development of specialty polymers with tailored properties for use in coatings, adhesives, and electronic materials.

Additionally, N-methylaminopropyltrimethoxysilane has applications in the field of chromatography. It is used in the preparation of functionalized stationary phases for chromatography columns, where its amine group can enhance the selectivity of the separation process. This application is particularly important in the separation of polar or basic compounds, where traditional silica-based stationary phases may not provide sufficient interaction with the sample.

In summary, N-methylaminopropyltrimethoxysilane is an important compound in various industrial applications, primarily due to its role as a coupling agent and surface modifier. Its ability to bond inorganic materials with organic components and to participate in further chemical reactions makes it invaluable in the production of advanced materials, coatings, adhesives, and composite materials. Its versatile chemical structure continues to make it a key component in the development of functionalized surfaces and hybrid materials across numerous industries.

References

1990. Thermomechanical Stability of Interphases in Glass Reinforced Composites. MRS Online Proceedings Library, 170.
DOI: 10.1557/proc-170-297

2019. Recent advances in development of amine functionalized adsorbents for CO2 capture. Adsorption, 25(7).
DOI: 10.1007/s10450-019-00151-0

2021. CO2 Hydrogenation over Ru-NPs Supported Amine-Functionalized SBA-15 Catalyst: Structure-Reactivity Relationship Study. Catalysis Letters, 151(10).
DOI: 10.1007/s10562-021-03609-5