Uses
3-Chloropropylamine hydrochloride was used in chemical treatment of carbon-enriched fly ash concentrates. It was used in the synthesis of linear, star and comb-like polyacrylamides by atomic transfer radical polymerization. It was used in the synthesis of halogen-functionalized aliphatic polyketones (macroinitiators).
Synthesis
General procedure for the synthesis of 3-chloropropylamine hydrochloride from 3-amino-1-propanol: An anhydrous chloroform (30 mL) solution of thionyl chloride (8.68 g, 1.32 mmol) was slowly added dropwise to 3-amino-1-propanol (4.49 g, 59.19 mmol) at 0-10°C. The reaction mixture was heated to room temperature and refluxed for 3 hours. The reaction mixture was gradually warmed to room temperature and then heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was collected by filtration to afford the target product 3-chloropropylamine hydrochloride (7.07 g, 55.15 mmol, 93% yield) as a green solid. Electrospray mass spectrometry (ESMS) showed m/z 94 ([M+H]+).
References
[1] Patent: WO2014/18571, 2014, A2. Location in patent: Paragraph 00463
[2] Patent: WO2014/18570, 2014, A1. Location in patent: Paragraph 00261
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5413 - 5417
[4] Angew. Chem., 2018, vol. 130, p. 5511 - 5515,5
