1-Adamantyltrimethylammonium hydroxide
[CAS# 53075-09-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: 1-Adamantyltrimethylammonium hydroxide
• Synonyms: N,N,N-Trimethyl-1-adamantammonium hydroxide; N,N,N-Trimethyl-1-
• Molecular Formula: C₁₃H₂₄N^.OH
• Molecular Weight: 211.35
• CAS Registry Number: 53075-09-5
• EC Number: 610-954-5
• SMILES: C[N+](C)(C)C12CC3CC(C1)CC(C3)C2.[OH-]

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H290-H302-H314-H318-H412
• Precautionary Statements: P234-P260-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402

Discovory and Applicatios

1-Adamantyltrimethylammonium hydroxide is a quaternary ammonium compound consisting of a nitrogen atom bonded to three methyl groups and one adamantyl group, with a hydroxide counterion. The adamantyl group, a bicyclic structure made of fused cyclohexane rings, imparts distinctive steric and electronic properties to the molecule. This substance is generally synthesized by reacting 1-bromoadamantane with trimethylamine, resulting in the formation of 1-adamantyltrimethylammonium hydroxide as a quaternary salt.

The compound is primarily utilized in organic synthesis, particularly in the context of phase transfer catalysis. In this application, 1-adamantyltrimethylammonium hydroxide serves as a phase transfer agent, facilitating the transfer of ionic species from one phase to another, typically from an aqueous phase to an organic phase. This property is useful in many reactions where ionic reactants need to interact with non-ionic reactants that are soluble only in organic solvents. As a phase transfer catalyst, it helps accelerate reactions like nucleophilic substitutions, making it valuable in the synthesis of various organic compounds.

1-Adamantyltrimethylammonium hydroxide is also employed in the synthesis of functionalized organic molecules. Its unique structure, with the bulky adamantyl group, provides steric hindrance that can influence the reactivity and selectivity of reactions. The presence of the hydroxide ion also allows for its use in reactions where the release or transfer of hydroxide is beneficial, such as in the formation of alcohols, ethers, and other oxygen-containing compounds.

Additionally, 1-adamantyltrimethylammonium hydroxide has found applications in ion-exchange processes and as a surfactant. The quaternary ammonium nature of the compound imparts amphiphilic characteristics, enabling it to stabilize emulsions and facilitate the solubilization of hydrophobic substances in aqueous solutions. This makes it useful in formulations like cleaning agents, detergents, and other industrial applications.

As with other quaternary ammonium compounds, 1-adamantyltrimethylammonium hydroxide should be handled with care. While it is generally considered to be of low toxicity, exposure may cause irritation to the skin, eyes, and respiratory system. Standard safety procedures, including the use of gloves, goggles, and appropriate ventilation, should be followed when handling this substance in laboratory or industrial settings.

In conclusion, 1-adamantyltrimethylammonium hydroxide is a versatile compound with significant applications in organic synthesis, phase transfer catalysis, and industrial processes. Its ability to facilitate the transfer of reactants between phases and its role in the synthesis of functionalized molecules and in surfactant formulations make it an important tool in various chemical processes. Its use in research and industry continues to highlight its value as a specialized reagent in modern chemistry.

References

2019 Palladium/Zeolite Low Temperature Passive NOx Adsorbers (PNA): Structure-Adsorption Property Relationships for Hydrothermally Aged PNA Materials. Emission Control Science and Technology, 1, 1.
DOI: 10.1007/s40825-019-00139-w

2019 Cu Loading Dependence of Fast NH3-SCR on Cu/SSZ-13. Emission Control Science and Technology, 1, 1.
DOI: 10.1007/s40825-019-00117-2

2018 Time-resolved copper speciation during selective catalytic reduction of NO on Cu-SSZ-13. Nature Catalysis, 1, 1.
DOI: 10.1038/s41929-018-0032-6