Bis(2-chloroethyl)amine hydrochloride Chemical Properties

Melting point:

212-214 °C(lit.)

storage temp. 

Store below +30°C.

solubility 

>100g/l

form 

Crystalline Powder

color 

White to beige

Water Solubility 

SOLUBLE

Sensitive 

Hygroscopic

BRN 

3550356

InChI

InChI=1S/C4H9Cl2N.ClH/c5-1-3-7-4-2-6;/h7H,1-4H2;1H

InChIKey

YMDZDFSUDFLGMX-UHFFFAOYSA-N

SMILES

N(CCCl)CCCl.Cl

CAS DataBase Reference

821-48-7(CAS DataBase Reference)

NIST Chemistry Reference

2,2'-Dichlorodiethylamine hydrochloride(821-48-7)

EPA Substance Registry System

Ethanamine, 2-chloro-N-(2-chloroethyl)-, hydrochloride (821-48-7)

Safety Information

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

MSDS

• Language:English Provider:Bis(2-chloroethyl)amine hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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

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