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| | Bis(2-chloroethyl)amine hydrochloride Basic information |
| | Bis(2-chloroethyl)amine hydrochloride Chemical Properties |
| Hazard Codes | Xi,T,C | | Risk Statements | 36/37/38-36-34 | | Safety Statements | 26-45-36/37/39-27 | | RIDADR | 2811 | | WGK Germany | 3 | | RTECS | IA1225000 | | Hazard Note | Irritant/Toxic | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29211980 | | Toxicity | LD50 orally in Rabbit: 1150 mg/kg |
| | Bis(2-chloroethyl)amine hydrochloride Usage And Synthesis |
| Chemical Properties | white to beige crystalline powder | | Uses | A cytotoxic metabolite of Cyclophosphamide; a deuterated analog of Nor-nitrogen mustard. | | Uses | Bis(2-chloroethyl)amine hydrochloride is used as an intermediate in chemicals synthesis and building block for piperazine derivatives. | | Safety Profile | 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-. | | Synthesis | 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. | | Purification Methods | 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, | | References | [1] Patent: US2015/299113, 2015, A1. Location in patent: Paragraph 0043
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 2, p. 231 - 234
[3] Patent: CN106397356, 2017, A. Location in patent: Paragraph 0045; 0060; 0066; 0074; 0082; 0090; 0098
[4] Patent: EP2682390, 2014, A1. Location in patent: Paragraph 0018; 0080
[5] Synthesis, 2010, # 16, p. 2705 - 2707 |
| | Bis(2-chloroethyl)amine hydrochloride Preparation Products And Raw materials |
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