Back أزيريدين Arabic Aziridin Azerbaijani آزیریدین AZB Этыленімін Byelorussian Aziridin BS Aziridina Catalan Aziridin Czech Aziridin German Αζιριδίνη Greek Aziridino Esperanto
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Aziridine | |||
| Systematic IUPAC name
Azacyclopropane | |||
| Other names
Azirane
Ethylenimine Aminoethylene Dimethyleneimine Dimethylenimine Ethylimine | |||
| Identifiers | |||
3D model (JSmol)
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| 102380 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.268 | ||
| EC Number |
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| 616 | |||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 1185 | ||
CompTox Dashboard (EPA)
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| 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
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highly flammable and toxic | ||
| GHS labelling: | |||
    
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| 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) | |||
| 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): | |||
LC50 (median concentration)
|
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] | ||
LCLo (lowest published)
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25 ppm (guinea pig, 8 hr) 56 ppm (rabbit, 2 hr)[4] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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OSHA-Regulated Carcinogen[2] | ||
REL (Recommended)
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Ca[2] | ||
IDLH (Immediate danger)
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Ca [100 ppm][2] | ||
| Related compounds | |||
Related heterocycles
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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 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.
- ^ "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.
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0274". National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ a b "Ethyleneimine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Gilchrist, T.L. (1987). Heterocyclic chemistry. Longman Scientific & Technical. ISBN 978-0-582-01421-3.
- ^ Epoxides and aziridines – A mini review Albert Padwa, S. Shaun Murphree Arkivoc (JC-1522R) pp. 6–33 Online article
- ^ Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_239.pub2. ISBN 3527306730.
- ^ 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.