white to beige crystalline powder
A cytotoxic metabolite of Cyclophosphamide; a deuterated analog of Nor-nitrogen mustard.
Bis(2-chloroethyl)amine hydrochloride is used as an intermediate in chemicals synthesis and building block for piperazine derivatives.
A poison by inhalation,intraperitoneal, intramuscular, and subcutaneous routes.An experimental teratogen. Human mutation datareported. When heated to decomposition it emits toxicfumes of NH3, NOx, and Cl-.
31.5 g (0.30 mol) of diethanolamine and 300 mL of dichloroethane were added to a 1 L round-bottomed flask equipped with a reflux condensing unit, followed by the slow dropwise addition of 51.0 mL of thionyl chloride. Immediately after the dropwise addition, the formation of a solid suspension was observed, and the suspension gradually dissolved as the temperature was raised to 50 °C. Stirring of the reaction mixture was continued under reflux conditions, during which the precipitation of crystalline solids was observed. Reflow was maintained and stirring was continued for 3 hours. Upon completion of the reaction, 20 mL of methanol was added to quench the reaction, followed by evaporation of the solvent under reduced pressure. The final white crystalline product bis(2-chloroethyl)amine hydrochloride was obtained in 53.0 g in quantitative yield.
Crystallise the salt from Me2CO or MeOH/Et2O. The picrate has m 112-113o (from EtOH or Me2CO). [Mann J Chem Soc 464 1934, Ward J Am Chem Soc 57 915 1935,
[1] Patent: US2015/299113, 2015, A1. Location in patent: Paragraph 0043
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[4] Patent: EP2682390, 2014, A1. Location in patent: Paragraph 0018; 0080
[5] Synthesis, 2010, # 16, p. 2705 - 2707
