Chemical Properties
2-Chloroethylamine hydrochloride (C2H7Cl2N, CAS registry No. 870-24-6) is a white to light beige crystalline powder. It is soluble in water and stable at room temperature in closed containers under normal storage and handling conditions. It should store in a tightly closed container, in a cool, dry, well-ventilated area away from incompatible substances and should be protected from moisture.
Application
2-Chloroethylamine hydrochloride is an important fine chemical intermediate. It can be used for the synthesis of fluvoxamine maleate, which is an important antidepressant drug. 2-Chloroethylamine hydrochloride can also be used as the substrate to synthesize 2-(2'-Aminoaryl)oxazolines and their derivatives, which have been studied as ligands for a variety of metal chelates and are known to possess biological activity in both free ligand and chelated forms. Meanwhile, 2-chloroethylamine hydrochloride can be used for chemical modification of chitosan to improve the biological activity of chitosan.
2-Chloroethylamine hydrochloride can also react with hydroxypropyl starch (HPS) to form aminoethyl hydroxypropyl starch (AEHPS), which can react with collagen peptide (COP) by using microbial transglutaminase (MTGase) as biocatalyst to synthesize aminoethyl hydroxypropyl starch collagen peptide (AEHPS-COP). The AEHPS-COP showed a promising potential application in cosmetic, biomedical and pharmaceutical fields with improved in vitro antioxidant activities.
Chemical Properties
WHITE TO LIGHT BEIGE CRYSTALLINE POWDER
Uses
2-Chloroethylamine hydrochloride can be used in the preparation of novel Schiff base ligands. These ligands, when immobilized on silica gels, form inexpensive materials for the removal of metal ions such as Ni
2+ and Co
2+ ions from contaminated water.
Other applications:- Alginate derivatization via aminoethylation to form aminoethyl alginate.
- Synthesis of N-(2-chloroethyl)-benzaldimine.
- Derivatization of starch to form aminoethyl (AE-St) starch derivatives.
Uses
2-chloroethylamine hydrochloride is used as an intermediate in active pharmaceutical ingredients and dyes. It is also used in organic synthesis. Further, it is employed as a derivatizing reagent for amino acids, dipeptides and nucleotides.
Synthesis
Example 7: 975 g of monoethanolamine hydrochloride, 3.7 g of dimethylformamide and 3500 g of benzene were mixed and heated to 75°C to 80°C. Subsequently, 1404 g of thionyl chloride was slowly added dropwise to the reaction mixture over 7 hours at the same temperature. After the dropwise addition was completed, the reaction was continued by keeping the reaction solution at the same temperature for 1 hour. Upon completion of the reaction, the mixture was cooled to 30°C and then 2900 g of water was added. After standing, the solution separated into a benzene layer and an aqueous layer. 4150 g of the aqueous layer was collected, which contained 2-chloroethylamine hydrochloride in 98% yield. The content of free sulfur dioxide in the aqueous layer was 2.7% by weight.
References
[1] Bulletin des Societes Chimiques Belges, 1984, vol. 93, # 10, p. 903 - 912
[2] Patent: US3956385, 1976, A
[3] Patent: CN105585607, 2016, A. Location in patent: Paragraph 0111; 0112; 0113; 0114
[4] Journal of Organic Chemistry, 1944, vol. 9, p. 137
[5] Journal of the American Chemical Society, 1935, vol. 57, p. 916
