HN1 (nitrogen mustard)
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| Names | |
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Preferred IUPAC name
2-Chloro-N-(2-chloroethyl)-N-ethylethan-1-amine
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| Other names
Bis(2-chloroethyl)(ethyl)amine
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3D model (JSmol)
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| ChemSpider | |
| MeSH | bis(2-chloroethyl)ethylamine |
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PubChem CID
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| RTECS number | YE1225000 |
| UN number | 2810 |
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| Properties | |
| C6H13Cl2N | |
| Molar mass | 170.08 g·mol−1 |
| Appearance | Colourless to pale yellow oily liquid |
| Odor | Fishy, musty |
| Density | 1.0861 g mL−1 (at 20 °C) |
| Melting point | −34 °C (−29 °F; 239 K) |
| Boiling point | 85.5 °C (185.9 °F; 358.6 K) |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a nitrogen mustard gas used for chemical warfare. HN1 was developed in the 1920s and 1930s to remove warts and later as a military agent. Because of the latter use, it is a Schedule 1 chemical within the Chemical Weapons Convention and therefore use and production is strongly restricted. It has never been used in warfare.
It is an oily liquid with a colorless to pale yellow appearance and a faint fishy or musty odor. HN1 is also an alkylating agent.
Nitrogen mustards react via an initial cyclization to the corresponding aziridinium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. The aziridinium ion reacts with water in a slower reaction. At pH 8, the nitrogen mustards are essentially quantitatively converted to the aziridinium ion for subsequent slow reaction with water. In contrast, at pH 4 cyclization and hydrolysis show the classic form of reactions in series. Hydrolysis of HN1 produces toxic intermediates.
HN1 reacts with iron alloys, corroding them at and above 65 °C (149 °F), and reacts with metals in general, producing hydrogen gas. This can potentially cause explosions.
Because HN1 is an alkylating agent, it damages DNA, causes immunosuppression, and causes injury to areas that come into contact with it. Exposure to HN1 can be fatal, and its effects on skin and mucous membranes are worsened when they are moist. The alkylation effects cause damage to the spleen, bone marrow, and lymph nodes, which causes anemia, low white cell counts, and internal bleeding. The vesicant effects cause blistering and damage to the skin.
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Wikipedia