Bis(2-chloroethyl)ethylamine

Bis(2-chloroethyl)ethylamine

IUPAC name	2-chloro-N-(2-chloroethyl)-N-ethyl-ethanamine; Compound 4644; ethyl-bis(-2-chloroethyl)amine; Bis-(2-chloroethyl)amine; HN1
Identifiers
CAS number	538-07-8
SMILES	ClCCN(CC)CCCl
Properties
Molecular formula	C₆H₁₃Cl₂N
Molar mass	170.08 g mol⁻¹
Density	1.0861 g/cm³ at 20°C, 1.09 at 25°C
Melting point	-34°C
Boiling point	85.5°C, 194°C decomposes
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Bis(2-chloroethyl)ethylamine is the organic compound with the formula C₂H₅N(CH₂CH₂Cl)₂. Often abbreviated HN1, it is a powerful vesicant and a so-called nitrogen mustard gas (it is not a gas) used for chemical warfare. HN-1 was developed in the 1920s and 1930s to remove warts and later as a military agent.

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Mode of action

Nitrogen mustards react via an initial cyclization to the corresponding iminium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. The iminium ion reacts with water in a slower reaction. At pH 8, the nitrogen mustards are essentially quantitatively converted to the iminium ion for subsequent slow reaction with water. In contrast, at pH 4 cyclization and hydrolysis show the classic form of reactions in series.