Tris(2-chloroethyl)amine

Chembox new
Name = Tris(2-chloroethyl)amine
ImageFile = Nitrogen-mustard-HN3.png ImageName = Tris(2-chloroethyl)amine
ImageFile1 = HN3-3D-vdW.png ImageName1 = Tris(2-chloroethyl)amine
IUPACName = 2-chloro-N,N-bis(2-chloroethyl)ethanamine
OtherNames = HN3, Compound 9560
Nitrogen mustard gas; tris-(2-chloroethyl)amine
trichlormethine; trimustine hydrochloride
Section1 = Chembox Identifiers
CASNo = 555-77-1
SMILES = ClCCN(CCCl)CCCl
Section2 = Chembox Properties
Formula = C₆H₁₂Cl₃N
MolarMass = 204.53 g mol⁻¹
Density = 1.24 g/cm³
MeltingPt = -3.7 to -4°C
BoilingPt = 143 °C

Tris(2-chloroethyl)ethylamine is the organic compound with the formula N(CH₂CH₂Cl)₃. Often abbreviated HN3, it is a powerful blister agent and a so-called nitrogen mustard gas (it is not a gas) used for chemical warfare. HN-3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of HD.

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.

Applications

HN-3 has found some applications in chemotherapy, e.g. for Hodgkin's disease, but it is mainly of interest for its military uses and is the only one of these agents that remains anywhere as a military agent. These agents are more immediately toxic than the sulfur mustards.

References