Dimethyldiethylammonium chloride
[CAS# 29508-45-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Dimethyldiethylammonium chloride
• Synonyms: N-Ethyl-N,N-dimethylethanaminium chloride
• Molecular Formula: C₆H₁₆N.Cl
• Molecular Weight: 137.65
• CAS Registry Number: 29508-45-0
• SMILES: CC[N+](C)(C)CC.[Cl-]

Discovery and Applications

Dimethyldiethylammonium chloride (C6H15ClN) is a quaternary ammonium salt, composed of a dimethyl group and a diethyl group attached to a nitrogen atom, along with a chloride anion. It is synthesized by the reaction of dimethylethanolamine with ethyl iodide.

This compound is commonly used in organic synthesis and as a phase-transfer catalyst. It has the ability to facilitate the movement of anionic species from aqueous solutions into organic solvents, thereby promoting a variety of chemical reactions that otherwise require high polarity solvents or special conditions. As a phase-transfer catalyst, dimethyldiethylammonium chloride helps accelerate reactions such as nucleophilic substitution and esterification by aiding in the transfer of reactants across the interface between two immiscible phases.

In addition to its role as a catalyst, it also finds application in the preparation of other chemical intermediates and in electrochemical processes. The substance is widely used in the manufacture of surfactants and other compounds in industrial applications. It has been studied for its potential utility in modifying the properties of materials and in enhancing the efficiency of certain synthetic processes.

Dimethyldiethylammonium chloride is typically handled with care due to its ionic nature and the potential for reactivity in certain conditions, though it is not considered particularly hazardous under standard laboratory conditions.

References

1983. Biodegradation and utilization of quaternary alkylammonium compounds by specialized methylotrophs. Cellular and Molecular Life Sciences, 39(11).
DOI: 10.1007/bf01990364