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Ethylenimine

Aziridine
Aziridine.svg
Aziridine3d.png
Names
IUPAC name
Aziridine
Other names
Azacyclopropane, Ethylene imine, Aminoethylene, Azirane, Dimethyleneimine, Dimethylenimine, Ethylimine
Identifiers
151-56-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:30969 YesY
ChEMBL ChEMBL540990 YesY
ChemSpider 8682 YesY
ECHA InfoCard 100.005.268
EC Number 205-793-9
KEGG C11687 YesY
Properties
C2H5N
Molar mass 43.07 g·mol−1
Appearance Clear colorless oily liquid
Odor ammonia-like
Density 0.8321 g/mL 20 °C
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)
Hazards
Main hazards highly flammable, very toxic
NFPA 704
Flammability code 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., gasoline) Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 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., fluorine Special hazards (white): no codeNFPA 704 four-colored 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):
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)
US health exposure limits (NIOSH):
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).
YesY  (what is YesYN ?)
Infobox references

Aziridines are organic compounds containing the aziridine functional group, a three-membered heterocycle with one amine group (-NH-) and two methylene bridges (-CH
2-). The parent compound is aziridine (or ethylene imine), with molecular formula C
2H
5N.

The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate invertomers, for example the cis and trans invertomers of N-chloro-2-methylaziridine.


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