Bis(2-chloroethyl)ethylamine

Bis(2-chloroethyl)ethylamine
HN1
IUPAC name 2-chloro-N-(2-chloroethyl)-N-ethyl-ethanamine; Compound 4644; ethyl-bis(-2-chloroethyl)amine; Bis-(2-chloroethyl)amine; HN1
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	538-07-8
PubChem	10848
ChemSpider	10391
SMILES
InChI
InChI key	UQZPGHOJMQTOHB-UHFFFAOYAK
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C6H13Cl2N
Molar mass	170.08 g mol−1
Density	1.0861 g/cm3 at 20°C, 1.09 at 25°C
Melting point	-34°C
Boiling point	85.5°C, 194°C decomposes
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 is an oily liquid with a colorless to pale yellow appearance and a faint fishy or musty odor.

Mode of action

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.

See also

• nitrogen mustard
• HN2 (mustine)
• HN3