Aziridine

Aziridine
Names
Preferred IUPAC name
Aziridine
Systematic IUPAC name
Azacyclopropane
Other names
Azirane
Ethylenimine
Aminoethylene
Dimethyleneimine
Dimethylenimine
Ethylimine
Identifiers
3D model (JSmol)
102380
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.268 Edit this at Wikidata
EC Number
  • 205-793-9
616
KEGG
RTECS number
  • KX5075000
UNII
UN number 1185
  • InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2 checkY
    Key: NOWKCMXCCJGMRR-UHFFFAOYSA-N checkY
  • InChI=1/C2H5N/c1-2-3-1/h3H,1-2H2
    Key: NOWKCMXCCJGMRR-UHFFFAOYAE
  • C1CN1
Properties
C2H5N
Molar mass 43.069 g·mol−1
Appearance Colorless oily liquid[1]
Odor ammonia-like[2]
Density 0.8321 g/mL 20 °C[3]
Melting point −77.9 °C (−108.2 °F; 195.2 K)
Boiling point 56 °C (133 °F; 329 K)
miscible
Vapor pressure 160 mmHg (20°C)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 highly flammable and toxic
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H300, H310, H314, H330, H340, H350, H411
P201, 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, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
4
3
3
Flash point −11 °C (12 °F; 262 K)
322 °C (612 °F; 595 K)
Explosive limits 3.6–46%
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)[4]
25 ppm (guinea pig, 8 hr)
56 ppm (rabbit, 2 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 OSHA-Regulated Carcinogen[2]
REL (Recommended)
 Ca[2]
IDLH (Immediate danger)
 Ca [100 ppm][2]
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).
checkY verify (what is checkY☒N ?)
For the general class, see Aziridines.

Aziridine is an organic compound consisting of the three-membered heterocycle C2H5N.[5][6] It is a colorless, toxic, volatile liquid that is of significant practical interest.[7] Aziridine was discovered in 1888 by the chemist Siegmund Gabriel.[8] Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

  1. ^ "Aziridine" (PDF). Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Vol. 71. 1999.
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0274". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Weast, Robert C.; et al. (1978). CRC Handbook of Chemistry and Physics (59th ed.). West Palm Beach, FL: CRC Press. ISBN 0-8493-0549-7.
  4. ^ a b "Ethyleneimine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Gilchrist, T.L. (1987). Heterocyclic chemistry. Longman Scientific & Technical. ISBN 978-0-582-01421-3.
  6. ^ Epoxides and aziridines – A mini review Albert Padwa, S. Shaun Murphree Arkivoc (JC-1522R) pp. 6–33 Online article
  7. ^ Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_239.pub2. ISBN 3527306730.
  8. ^ Gabriel, S. (1888). "Ueber Vinylamin und Bromäthylamin. (II.)". Berichte der Deutschen Chemischen Gesellschaft. 21 (2): 2664–2669. doi:10.1002/cber.18880210287. ISSN 1099-0682.