2-Dimethylaminoethyl chloride hydrochloride
[CAS# 4584-46-7]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 2-Dimethylaminoethyl chloride hydrochloride
• Synonyms: 2-chloroethyldimethylammonium chloride; 2-Chloro-N,N-dimethylethylamine hydrochloride; N,N-Dimethylamino chloroethane hydrochloride
• Molecular Formula: C₄H₁₀ClN.HCl;C₄H₁₁Cl₂N
• Molecular Weight: 144.04
• CAS Registry Number: 4584-46-7
• EC Number: 224-970-1
• SMILES: CN(C)CCCl.Cl

Properties

• Melting point: 205-208 °C
• Water solubility: 2000 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H301-H302-H311-H315-H319-H335-H341-H373-H411
• Safety Statements: P203-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P318-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	1	H330
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	2	H371

• Transport Information: UN 2811

Discovery and Applications

2-Dimethylaminoethyl chloride hydrochloride is an important quaternary ammonium compound widely utilized in organic synthesis and medicinal chemistry. The compound is derived from the reaction of dimethylaminoethyl chloride with hydrochloric acid, resulting in a stable hydrochloride salt. Its discovery is attributed to the broader interest in aminoalkyl halides and their derivatives in the early to mid-20th century, which coincided with the expansion of chemical research focused on the synthesis of biologically active compounds.

The synthesis of 2-dimethylaminoethyl chloride hydrochloride involves the reaction of 2-dimethylaminoethanol with thionyl chloride or hydrochloric acid. This reaction leads to the formation of the corresponding alkyl chloride, which is then converted to the hydrochloride salt. The resulting compound exhibits a high degree of solubility in water, making it particularly useful in various applications.

One of the primary applications of 2-dimethylaminoethyl chloride hydrochloride is as a building block in the synthesis of pharmaceuticals and bioactive molecules. Its amine functionality allows for the formation of various derivatives through nucleophilic substitution reactions. This reactivity is leveraged in the development of compounds with potential therapeutic applications, particularly in the field of central nervous system agents, where it serves as a precursor for the synthesis of antihistamines and antidepressants.

Additionally, 2-dimethylaminoethyl chloride hydrochloride is employed in the synthesis of surfactants and polymers. The quaternary ammonium structure imparts surface-active properties, making it useful in the formulation of detergents, emulsifiers, and other industrial applications. Its ability to interact with both polar and non-polar molecules enhances the performance of formulations in various sectors, including personal care and household products.

In the field of biochemistry, 2-dimethylaminoethyl chloride hydrochloride has gained attention for its role as a reagent in the preparation of cationic lipids for gene delivery systems. These lipids are used to create liposomes that facilitate the transport of nucleic acids into cells, a vital process in gene therapy and vaccine development. The incorporation of the dimethylaminoethyl group enhances the lipophilicity and positive charge of the lipids, improving their efficacy in cellular uptake.

Recent studies have also explored the potential of 2-dimethylaminoethyl chloride hydrochloride in the development of novel antimicrobial agents. Research indicates that quaternary ammonium compounds possess antimicrobial properties, and derivatives of 2-dimethylaminoethyl chloride have shown promise in combating various pathogens, thereby contributing to the ongoing search for effective alternatives to traditional antibiotics.

In summary, 2-dimethylaminoethyl chloride hydrochloride is a significant compound with a rich history and diverse applications in organic synthesis, pharmaceuticals, and materials science. Its discovery has paved the way for advancements in various fields, and ongoing research continues to uncover new potential uses for this versatile compound.

References

2024. Introducing Propionate and 2-Dimethylammonium Chloride Ethyl Substituents onto Cornstarch for Acquiring Good Film Properties and Easy Desizing from Sized Warps. Fibers and Polymers, 25(2).
DOI: 10.1007/s12221-024-00476-w

2023. Introduction of N,N-Dimethylaminoethyls onto Maize Starch for Strong Bonding and Easy Removal for Polyester Warp Sizing. Fibers and Polymers, 24(4).
DOI: 10.1007/s12221-023-00101-2

1997. Synthesis of new alkyl maleates ammonium derivatives and their uses in emulsion polymerization. Colloid and Polymer Science, 275(1).
DOI: 10.1007/s003960050046