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Aziridination

Aziridine
Aziridine.svg
Aziridine3d.png
Names
IUPAC name
Aziridine
Other names
Azacyclopropane, Ethylene imine, Aminoethylene, Azirane, Dimethyleneimine, Dimethylenimine, Ethylimine
Identifiers
3D model (JSmol)
102380
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.268
EC Number 205-793-9
616
KEGG
PubChem CID
RTECS number KX5075000
UNII
UN number 1185
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
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H225, H300, H310, H314, H318, H330, H340, H350, H411
P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+310, P301+330+331, P302+350, P303+361+353, P304+340, P305+351+338, P308+313, P310
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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