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2-Chloroethylamine hydrochloride: Introduction, Application and Synthesis

Oct 9，2024

What is 2-Chloroethylamine hydrochloride?

2-Chloroethylamine hydrochloride is an organic salt compound used primarily in organic synthesis, but also as an intermediate in active pharmaceutical ingredients and dyes. In addition, it is used as a derivatisation reagent for amino acids, dipeptides and nucleotides. In the field of materials, hydrothermal pre-reduction of graphene oxide (GO) with 2-chloroethylamine hydrochloride results in a more ordered structure of the material, which is associated with good electronic conductivity and higher basicity.

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Application

A chemoselective route to thiazolines and thiazines has been devised by heterocyclization of viable α-N-hydroxyimino-β-oxodithioesters with 2-chloroethylamine hydrochloride/3-chloropropylamine hydrochloride, which does not require metals or additives and proceeds at 0–60 °C. The overall transformation involves base mediated intramolecular cyclization of α-N-hydroxyimino-β-oxodithioesters to 4-membered oxazete-4-thione intermediates followed by coupling with chloroalkyl amines via tandem ring cleavage and C−N/C−S bonds formation enabling the construction of thiazolines/thiazines in one-pot. This strategy allows broadening the arsenal of synthetic methods to obtain N,S-heterocycles utilizing substrates prepared according to reported procedures.

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The amination of kraft lignin by using 2-Chloroethylamine hydrochloride in an aqueous solvent can be used to prepare an aminated lignin-silver complex (Ag@AL complex) as an alternative antimicrobial agent. The optimised AL had a nitrogen content of 4.37%.Ag(Ⅰ) could be trapped by AL and reduced to the metal Ag(0), resulting in the formation of AgNPs on the surface of AL. Importantly, the obtained Ag@AL complex proved to be an effective antimicrobial agent against both Gram-positive (Bacillus cereus, Staphylococcus aureus) and Gram-negative bacteria (Salmonella enteritidis).

Synthesis

2-Chloroethylamine hydrochloride can be produced by reacting 2-hydroxyethylamine hydrochloride with thionyl chloride in the presence of a solvent. This is characterised by the use of an aliphatic carboxylic acid or a mixture of aliphatic carboxylic acids with a chain length of 1 to 10 C- as the solvent.

References:

[1] M. PINZÓN . New catalysts based on reduced graphene oxide for hydrogen production from ammonia decomposition[J]. Sustainable Chemistry and Pharmacy, 2022. DOI:10.1016/j.scp.2022.100615.

[2] SUBHASISH RAY. Reagent-Controlled Chemodivergent Approach to Thiazolines and Thiazines from α-N-Hydroxyimino Dithioesters[J]. Advanced Synthesis & Catalysis, 2022. DOI:10.1002/adsc.202200511.

[3] JIANSONG CHEN . Green and facile synthesis of aminated lignin-silver complex and its antibacterial activity[J]. Industrial Crops and Products, 2021. DOI:10.1016/j.indcrop.2021.114102.

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