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| Names | |
|---|---|
| Preferred IUPAC name 2-Chloro-N,N-bis(2-chloroethyl)ethanamine | |
| Other names Trichlormethine Tris(2-chloroethyl)amine EA-1053 TL-145 | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| MeSH | 2,2',2+-trichlorotriethylamine |
| UNII | |
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| Properties | |
| C6H12Cl3N | |
| Molar mass | 204.52 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Fishy, ammoniacal |
| Density | 1.24 g mL−1 |
| Melting point | −4 to −3.7 °C (24.8 to 25.3 °F; 269.1 to 269.4 K) |
| Boiling point | 143 °C (289 °F; 416 K) |
| logP | 1.306 |
| Related compounds | |
Related amines | |
Related compounds | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2-Chloro-N,N-bis(2-chloroethyl)ethanamine, also known astrichlormethine,tris(2-chloroethyl)amine is theorganic compound with theformula N(CH2CH2Cl)3. Often abbreviated HN3 or HN-3, it is a powerfulblister agent and anitrogen mustard used forchemical warfare. HN3 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 ofHD and thus the analogy between the two types of mustard is the strongest.[1] As avesicant the use and production is strongly restricted within theChemical Weapons Convention where it is classified as aSchedule 1 substance.
Nitrogen mustards react via an initial cyclization to the corresponding quaternaryaziridine salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize.
HN-3 has found some applications in chemotherapy, e.g., forHodgkin's disease, and in some compound semiconductor research[2] 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.[citation needed] These agents are more immediately toxic than thesulfur mustards.
HN-3 can be absorbed into the body by inhalation, ingestion, eye contact, and skin contact (though inhalation is the most common). The chemical is extremely toxic and may damage the eyes, skin, and respiratory tract and suppress the immune system. HN-3 penetrates and binds quickly to cells of the body, but its health effects develop slowly. The full extent of cellular injury may not be known for days.[1]
