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Aziridine

Organic ring compound with the formula (CH2)2NH From Wikipedia, the free encyclopedia

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.

Quick Facts Names, Identifiers ...
Aziridine
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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)
102380
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.268
EC Number
  • 205-793-9
616
KEGG
RTECS number
  • KX5075000
UNII
UN number 1185
  • InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2 Y
    Key: NOWKCMXCCJGMRR-UHFFFAOYSA-N Y
  • 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)
ThumbHealth 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).
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For the general class, see Aziridines.

Structure

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.

Synthesis and uses

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Linear polyethylenimine (PEI) fragment, derived from aziridine.
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Typical branched PEI fragment, derived from aziridine.

Aziridine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to effect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base-induced sulfate elimination. Older methods entailed amination of 1,2-dichloroethane and cyclization of 2-chloroethylamine.[7]

Aziridine forms a wide variety of polymeric derivatives, known as polyethylenimines (PEI). These and related species are useful crosslinking agents and precursors for coatings.[7]

Safety

Aziridine is highly toxic with an LD50 of 14 mg (oral, rats). It is a skin irritant. As an alkylating agent, it is also a mutagen.[7] It is reactive toward DNA, potentially relevant to its mutagenicity. Aziridine containing compounds also appear to be similarly dangerous.[9][10][11]

See also

References

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