2-Diethylaminoethylchloride hydrochloride
[CAS# 869-24-9]

Identification

• Classification: Organic raw materials >> Amino compound
• Name: 2-Diethylaminoethylchloride hydrochloride
• Synonyms: 2-Chloro-N,N-diethylethaneamine hydrochloride; 2-Chlorotriethylamine hydrochloride; DEC
• Molecular Formula: C₆H₁₄ClN^.HCl
• Molecular Weight: 172.10
• CAS Registry Number: 869-24-9
• EC Number: 212-786-4
• SMILES: CCN(CC)CCCl.Cl

Properties

• Melting point: 208-212 ºC
• Water solubility: 2000 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H300+H310+H330-H300-H310-H314-H315-H319-H330-H335-H341-H411-H412
• Precautionary Statements: P203-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P318-P319-P320-P321-P330-P332+P317-P361+P364-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	2	H330
Germ cell mutagenicity	Muta.	2	H341
Skin corrosion	Skin Corr.	1B	H314
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	1	H330
Carcinogenicity	Carc.	2	H351
Skin corrosion	Skin Corr.	1	H314
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	1	H300

• Transport Information: UN 2811

Discovory and Applicatios

2-Diethylaminoethylchloride hydrochloride is an organic compound with the molecular formula C6H14ClN, recognized as a quaternary ammonium salt. It features a diethylamino group attached to a two-carbon ethyl chain, making it a derivative of 2-aminoethyl chloride. The discovery of this compound can be traced back to the early 20th century when chemists began exploring the synthesis of aminoalkyl compounds for various applications in medicinal chemistry and organic synthesis.

The compound is primarily synthesized through the reaction of diethylamine with 1,2-dichloroethane or related chlorinated hydrocarbons, leading to the formation of 2-dialkylaminoethylchloride. The hydrochloride form is obtained by treating the base with hydrochloric acid, which enhances its solubility and stability in various solvents, making it suitable for laboratory and industrial applications.

One of the notable applications of 2-diethylaminoethylchloride hydrochloride is in the field of pharmaceuticals. It serves as an important intermediate in the synthesis of various bioactive compounds, including local anesthetics, muscle relaxants, and antihistamines. Its ability to modify the properties of target molecules by introducing a quaternary ammonium group has made it a valuable building block in medicinal chemistry. Furthermore, it is used in the preparation of surfactants, which are crucial in formulating pharmaceuticals, personal care products, and agricultural chemicals.

In addition to its pharmaceutical applications, 2-diethylaminoethylchloride hydrochloride is utilized in the synthesis of polymeric materials and as a reagent in organic synthesis. It can participate in nucleophilic substitution reactions, allowing for the introduction of various functional groups into organic molecules. This versatility makes it an essential compound in the development of novel materials and fine chemicals.

The compound also exhibits biological activity, with studies indicating its potential as an antimicrobial and antifungal agent. Research into its biological properties has opened avenues for further exploration of its applications in medicine and agriculture, particularly in developing new therapeutic agents and formulations.

Despite its utility, caution is advised when handling 2-diethylaminoethylchloride hydrochloride due to its potential irritant properties. It may cause skin and eye irritation upon contact, and inhalation of its dust or vapors should be avoided. Proper laboratory safety protocols, including the use of personal protective equipment, should be observed when working with this compound.

In summary, 2-diethylaminoethylchloride hydrochloride is a significant compound with a rich history of discovery and diverse applications in pharmaceuticals, organic synthesis, and materials science. Its ability to modify the properties of various molecules and its potential biological activities underscore its importance in various scientific fields. Ongoing research into its properties and applications continues to reveal new opportunities for this versatile compound.

References

2018. Synthesis of N1,N1,N3,N3-tetrasubstituted diethylenetriamines. Russian Chemical Bulletin, 67(5).
DOI: 10.1007/s11172-018-2147-y

2016. Textile cotton dust waste: partial diethylaminoethylation and its application to the sorption/removal of the model residual textile dye Reactive Red 239. Polymer Bulletin, 73(11).
DOI: 10.1007/s00289-016-1663-x

2014. Regioselective synthesis of 6-amino- and 6-amido-6-deoxypullulans. Cellulose, 21(4).
DOI: 10.1007/s10570-014-0259-6