View source for Tris(2-chloroethyl)amine

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! {{chembox header}}| '''Tris(2-chloroethyl)amine''' <!-- replace if not identical with the article name -->
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nitrogen-mustard-HN3.png|200px|Tris(2-chloroethyl)amine]]<br>
[[Image:HN3-3D-vdW.png|200px|Tris(2-chloroethyl)amine]]
|-
| [[IUPAC nomenclature|Chemical name]]
| 2-chloro-N,N-bis(2-chloroethyl)ethanamine
|-
| Other names
| HN3, Compound 9560<br/>Nitrogen mustard gas; tris-(2-chloroethyl)amine<br/>trichlormethine; trimustine hydrochloride
|-
| [[Chemical formula]]
| C<sub>6</sub>H<sub>12</sub>Cl<sub>3</sub>N
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| [[Molecular mass]]
| 204.53 g mol<sup>−1</sup>
|-
| [[CAS registry number|CAS number]]
| [555-77-1]
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| [[Density]]
| 1.24 g/cm<sup>3</sup>
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| [[Melting point]]
| -3.7 to -4°C
|-
| [[Boiling point]]
| 143 °C
|-
| [[Simplified molecular input line entry specification|SMILES]]
| ClCCN(CCCl)CCCl
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
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|}
{{SI}}


==Overview==
'''Tris(2-chloroethyl)ethylamine''' is the [[organic compound]] with the [[Chemical formula|formula]] N(CH<sub>2</sub>CH<sub>2</sub>Cl)<sub>3</sub>.  Often abbreviated HN3, it is a  powerful [[vesicant|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.


{{Chemical warfare}}

[[Category:Chemotherapeutic agents]]
[[Category:Amines]]
{{WH}}
{{WS}}