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Bis(2-chloroethyl)amine hydrochloride

Product NameBis(2-chloroethyl)amine hydrochloride
CAS821-48-7
MFC4H10Cl3N
MW178.49
EINECS212-479-5
MOL File821-48-7.mol

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	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29211980
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Met. Corr. 1 Skin Corr. 1B
Toxicity	LD50 orally in Rabbit: 1150 mg/kg

MSDS

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

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

111-42-2

821-48-7

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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