Topic summary

Aziridine

Aziridine
Names Preferred IUPAC name
Aziridine
Systematic IUPAC name
Azacyclopropane
Other names
Azirane
Ethylenimine
Aminoethylene
Dimethyleneimine
Dimethylenimine
Ethylimine
Identifiers
3D model (JSmol)
102380 ChEBIChEMBLChemSpiderECHA InfoCard100.005.268EC Number
  • 205-793-9
616 KEGGRTECS number
  • KX5075000
UNIIUN number1185
  • InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
    Key: NOWKCMXCCJGMRR-UHFFFAOYSA-N
  • InChI=1/C2H5N/c1-2-3-1/h3H,1-2H2
    Key: NOWKCMXCCJGMRR-UHFFFAOYAE
  • C1CN1
Properties C2H5NMolar mass43.069 g·mol Appearance Colorless oily liquid Odorammonia-like Density0.8321 g/mL 20 °C Melting point−77.9 °C (−108.2 °F; 195.2 K) Boiling point56 °C (133 °F; 329 K) miscible Vapor pressure160 mmHg (20°C) Hazards Occupational safety and health (OHS/OSH):
Main hazards
highly flammable and toxic GHS labelling: DangerH225, H300, H310, H314, H330, H340, H350, H411P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501NFPA 704 (fire diamond) Flash point−11 °C (12 °F; 262 K) 322 °C (612 °F; 595 K) Explosive limits3.6–46% Lethal dose or concentration (LD, LC): 250 ppm (rat, 1 hr)
250 ppm (guinea pig, 1 hr)
62 ppm (rat, 4 hr)
223 ppm (mouse, 2 hr)
56 ppm (rat, 2 hr)
2236 ppm (mouse, 10 min) 25 ppm (guinea pig, 8 hr)
56 ppm (rabbit, 2 hr) NIOSH (US health exposure limits):
PEL (Permissible)
OSHA-Regulated Carcinogen
REL (Recommended)
Ca
IDLH (Immediate danger)
Ca [100 ppm] Related compounds
Related heterocycles
Borirane
Ethylene oxide
Thiirane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Aziridine is an organic compound consisting of the three-membered heterocycleC2H5N. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.