2-Chloroethylamine hydrochloride
[CAS# 870-24-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 2-Chloroethylamine hydrochloride
• Synonyms: 2-Aminoethyl chloride hydrochloride
• Molecular Formula: C₂H₆ClN.HCl;C₂H₇Cl₂N
• Molecular Weight: 115.99
• CAS Registry Number: 870-24-6
• EC Number: 212-793-2
• SMILES: C(CCl)N.Cl

Properties

• Melting point: 140-150 °C
• Water solubility: SOLUBLE

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H290-H314-H315-H319-H335-H341
• Safety Statements: P203-P234-P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P318-P319-P321-P332+P317-P337+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	2	H341
Skin corrosion	Skin Corr.	1C	H314
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

Discovery and Applications

2-Chloroethylamine hydrochloride, a significant organic compound in medicinal chemistry, was first synthesized in the early 20th century during studies on alkylating agents. With the molecular formula C2H7Cl2N, it consists of an ethylamine chain where one hydrogen atom is replaced by a chlorine atom. Its hydrochloride form increases its stability and solubility in water. The discovery of 2-chloroethylamine hydrochloride was pivotal, as it became a key intermediate in the synthesis of various therapeutic agents, particularly in the development of alkylating agents for cancer treatment.

2-Chloroethylamine hydrochloride is a valuable intermediate in pharmaceutical synthesis, particularly in the production of alkylating agents. These agents are used in chemotherapy to treat various types of cancer. The compound's ability to form covalent bonds with DNA makes it effective in inhibiting cancer cell proliferation. Its derivatives, such as mustards and related compounds, have been foundational in cancer treatment protocols.

In chemical research, 2-chloroethylamine hydrochloride is used as a building block for synthesizing more complex molecules. Its reactivity allows for the introduction of the 2-chloroethyl group into various chemical structures, facilitating the development of new compounds with potential biological activity.

2-Chloroethylamine hydrochloride is used in the synthesis of certain agrochemicals, including herbicides and pesticides. Its alkylating properties are harnessed to develop compounds that can control or eliminate pests and weeds, improving crop yields and agricultural productivity.

In polymer chemistry, 2-chloroethylamine hydrochloride is used to modify polymer chains, imparting specific properties such as increased reactivity or cross-linking ability.

The compound is also employed in biochemical studies to investigate the mechanisms of alkylation and its effects on biological molecules. By studying the interactions of 2-chloroethylamine hydrochloride with DNA and proteins, scientists gain insights into the molecular basis of its therapeutic effects and potential side effects.

References

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

2017. Novel approach to the synthesis of istaroxime. Russian Journal of General Chemistry, 87(11).
DOI: 10.1134/s1070363217110196

1946. CHEMICAL REACTIONS OF THE NITROGEN MUSTARD GASES. I. THE TRANSFORMATIONS OF METHYL-BIS(β-CHLOROETHYL)AMINE IN WATER. The Journal of Organic Chemistry, 11(5).
DOI: 10.1021/jo01175a015