Tris(2-chloroethyl)amine

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Tris(2-chloroethyl)amine
Tris(2-chloroethyl)amine

Tris(2-chloroethyl)amine

Chemical name 2-chloro-N,N-bis(2-chloroethyl)ethanamine
Other names HN3, Compound 9560
Nitrogen mustard gas; tris-(2-chloroethyl)amine
trichlormethine; trimustine hydrochloride
Chemical formula C6H12Cl3N
Molecular mass 204.53 g mol−1
CAS number [555-77-1]
Density 1.24 g/cm3
Melting point -3.7 to -4°C
Boiling point 143 °C
SMILES ClCCN(CCCl)CCCl
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Overview

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.

Safety

Like other chemical warfare agents, tris92-chloroethyl)amine is highly toxic.




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