Bis(2-chloroethyl)ethylamine

Chembox new
Name = Bis(2-chloroethyl)ethylamine
ImageFile = Nitrogen-mustard-HN1.png ImageName = HN1
IUPACName = 2-chloro-N-(2-chloroethyl)-N-ethyl-ethanamine; Compound 4644; ethyl-bis(-2-chloroethyl)amine; Bis-(2-chloroethyl)amine; HN1
Section1 = Chembox Identifiers
CASNo = 538-07-8
SMILES = ClCCN(CC)CCCl
Section2 = Chembox Properties
Formula = C₆H₁₃Cl₂N
MolarMass = 170.08 g mol⁻¹
Density = 1.0861 g/cm³ at 20°C, 1.09 at 25°C
MeltingPt = -34°C
BoilingPt = 85.5°C, 194°C decomposes

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.

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.

References