Tetraethyl ammonium chloride
[CAS# 56-34-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Tetraethyl ammonium chloride
• Synonyms: Tetraethylammonium chloride; TEA chloride
• Molecular Formula: C₈H₂₀N^.Cl
• Molecular Weight: 165.70
• CAS Registry Number: 56-34-8
• EC Number: 200-267-5
• SMILES: CC[N+](CC)(CC)CC.[Cl-]

Properties

• Solubility: 100 mM (water) (Expl.)
• Density: 1.08 g/mL (Expl.)
• Melting point: 110 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-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
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovory and Applicatios

Tetraethylammonium chloride is a quaternary ammonium salt composed of a central nitrogen atom bonded to four ethyl groups and chloride as the counterion. It is commonly synthesized by reacting ethyl iodide with tetraethylammonium hydroxide or through other methods involving the alkylation of amines. Tetraethylammonium chloride appears as a white crystalline solid and is highly soluble in water and ethanol.

This compound has found widespread use in both research and industrial applications, primarily due to its role in ion exchange processes and as a phase transfer catalyst. As a quaternary ammonium compound, tetraethylammonium chloride exhibits amphiphilic characteristics, which allow it to interact with both polar and non-polar substances. This property makes it useful in facilitating the transport of ions across immiscible solvents in chemical reactions, particularly in organic synthesis.

In the field of organic chemistry, tetraethylammonium chloride is often employed as a phase transfer catalyst. It helps accelerate reactions by promoting the interaction between ionic species that would otherwise be limited to aqueous solutions and non-ionic reactants that are soluble in organic solvents. This enhances the efficiency of reactions like nucleophilic substitutions and helps drive certain reactions to completion by overcoming phase boundary limitations. Tetraethylammonium chloride is also used in the synthesis of various organic compounds and intermediates, facilitating reactions that require the transfer of reactants between different phases.

Moreover, tetraethylammonium chloride has been explored in research related to its ability to interact with biological systems. It is sometimes utilized in studies involving membrane transport and in the investigation of its potential effects on cellular processes due to its quaternary ammonium nature. In some cases, tetraethylammonium chloride is used to block ion channels or to modulate the activity of certain enzymes and receptors, providing insights into the role of ionic movements in biological systems.

Additionally, tetraethylammonium chloride has applications in the preparation of other tetraethylammonium salts, which are used in a variety of chemical processes. It can serve as a precursor for producing tetraethylammonium hydroxide, which has similar applications in organic synthesis and phase transfer catalysis.

While tetraethylammonium chloride is considered to be relatively stable, it should be handled with care due to the potential toxicity of quaternary ammonium compounds. It may cause irritation upon contact with the skin or eyes, and proper safety precautions should be taken when working with this substance in laboratory or industrial settings.

In summary, tetraethylammonium chloride is an important chemical compound with diverse applications in organic synthesis, phase transfer catalysis, and research. Its ability to facilitate ion transport across phases and its utility in synthesizing organic molecules make it a valuable reagent in various chemical processes. Its role in membrane transport and biological studies further highlights its significance in scientific research.

References

2024 Thermally induced neuronal plasticity in the hypothalamus mediates heat tolerance. Nature Neuroscience, 1, 1.
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2024 Nitric Oxide and Small and Intermediate Calcium-Activated Potassium Channels Mediate the Vasodilation Induced by Apigenin in the Resistance Vessels of Hypertensive Rats. Molecules (Basel, Switzerland), 1, 1.
DOI: 10.3390/molecules29225425

2024 Small-molecule natural product sophoricoside reduces peripheral neuropathic pain via directly blocking of NaV1.6 in dorsal root ganglion nociceptive neurons. Neuropsychopharmacology, 1, 1.
DOI: 10.1038/s41386-024-01998-w