Tetraethylammonium tosylate
[CAS# 733-44-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Tetraethylammonium tosylate
• Synonyms: Tetraethylammonium p-toluenesulfonate
• Molecular Formula: C₈H₂₀N.C₇H₇O₃S
• Molecular Weight: 301.44
• CAS Registry Number: 733-44-8
• EC Number: 211-992-1
• SMILES: CC[N+](CC)(CC)CC.CC1=CC=C(C=C1)S(=O)(=O)[O-]

Properties

• Melting point: 110-114 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

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
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Tetraethylammonium tosylate, with the chemical formula C₈H₂₀NO₃S, is an organic compound that consists of a tetraethylammonium cation paired with a tosylate anion. It is a quaternary ammonium salt commonly used in organic chemistry and various synthetic applications. The compound is recognized for its ability to facilitate nucleophilic substitution reactions and has been widely utilized in the synthesis of various chemicals.

The discovery of tetraethylammonium tosylate can be traced to the continued development and exploration of quaternary ammonium salts in the mid-20th century. Quaternary ammonium salts, such as tetraethylammonium tosylate, are known for their ionic nature and the ability to act as phase-transfer catalysts. These compounds became increasingly valuable in synthetic chemistry due to their ability to enhance the reactivity of otherwise less reactive nucleophiles.

Tetraethylammonium tosylate is most commonly employed in organic synthesis, where it acts as a phase-transfer catalyst, promoting reactions that occur between reactants in different phases. In particular, it is frequently used in the preparation of other quaternary ammonium salts and in the synthesis of organic compounds that require the migration of ions between different phases. The tosylate anion (p-toluenesulfonate) is often chosen because it is a good leaving group in nucleophilic substitution reactions, making tetraethylammonium tosylate useful in the generation of alkylated products.

One of the key applications of tetraethylammonium tosylate is in the synthesis of alkylated organic compounds. The compound is often used in reactions where an alkyl group is transferred from the tetraethylammonium cation to a substrate molecule. This type of reaction is commonly used to introduce functional groups into organic molecules, which is essential for the creation of more complex molecules. For example, tetraethylammonium tosylate can be used in the synthesis of various alkyl esters, ethers, and other organic derivatives.

Tetraethylammonium tosylate is also utilized in research as a reagent in the synthesis of organic compounds. Its ability to facilitate nucleophilic substitutions makes it an important tool in the synthesis of compounds with specific functional groups. Additionally, the compound is employed in studies involving ion exchange processes and in applications where its quaternary ammonium structure is valuable for creating ionic interactions or acting as a solubility enhancer.

In the realm of biochemistry and pharmacology, tetraethylammonium tosylate has been studied for its role in biological systems, especially as a model compound to understand the behavior of quaternary ammonium ions in various environments. However, its primary use remains within chemical synthesis rather than direct biological applications.

The use of tetraethylammonium tosylate is also notable in the study of organic mechanisms. In particular, it is used to explore the effects of phase-transfer catalysis, where the solubility of reagents in different phases is crucial for achieving high reaction efficiency. This application is important in industrial-scale reactions, where the separation of phases is often a challenge, and tetraethylammonium tosylate helps facilitate the transfer of ions between aqueous and organic phases, thus accelerating reactions that would otherwise be slow.

In conclusion, tetraethylammonium tosylate is an important chemical compound in organic synthesis, primarily used as a phase-transfer catalyst and reagent in nucleophilic substitution reactions. Its applications in the synthesis of alkylated organic compounds, in the study of ion exchange processes, and as a tool in the exploration of organic reaction mechanisms, make it a valuable substance in both academic and industrial chemistry.

References

2024. Electrochemical conversion of organic compounds and inorganic small molecules. Science China Chemistry, 67(8).
DOI: 10.1007/s11426-024-2036-0

2024. Modern electrosynthesis of spiro compounds. Russian Chemical Bulletin, 73(7).
DOI: 10.1007/s11172-024-4303-x

2023. Photoelectrochemical asymmetric dehydrogenative [2 + 2] cycloaddition between C-C single and double bonds via the activation of two C(sp3)-H bonds. Nature Catalysis, 6(11).
DOI: 10.1038/s41929-023-01050-y