Aziridine

From Wikipedia, the free encyclopedia

Template:Short description Page Template:Chembox/styles.css has no content.

Template:Chembox IndexlistTemplate:Chembox ECHATemplate:Chembox CompToxTemplate:Chembox OHS (set)Template:Chembox GHS (set)Template:Chembox Datapage check
Aziridine
Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found.
Names
Preferred IUPAC name
Aziridine
Systematic IUPAC name
Azacyclopropane
Other names
Azirane
Ethylenimine
Aminoethylene
Dimethyleneimine
Dimethylenimine
Ethylimine
Identifiers
Page Template:Plainlist/styles.css has no content.
3D model (JSmol)
 Page Template:Plainlist/styles.css has no content.
102380
ChEBI Page Template:Plainlist/styles.css has no content.
ChEMBL Page Template:Plainlist/styles.css has no content.
ChemSpider Page Template:Plainlist/styles.css has no content.
EC Number Page Template:Plainlist/styles.css has no content.
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
616
KEGG Page Template:Plainlist/styles.css has no content.
Page Template:Plainlist/styles.css has no content.
RTECS number Page Template:Plainlist/styles.css has no content.
UNII Page Template:Plainlist/styles.css has no content.
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
NFPA 704 (fire diamond) Page Template:NFPA 704 diamond/styles.css has no content.
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 ?)

Template:Chembox Footer/trackingTemplate:Short description

Script error: No such module "For".

Aziridine is an organic compound consisting of the three-membered heterocycle Page Module:Chem2/styles.css has no content.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.

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

Page Template:Multiple image/styles.css has no content.

Linear polyethylenimine (PEI) fragment, derived from aziridine.
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

Page Template:Reflist/styles.css has no content.

  1. ^ Page Module:Citation/CS1/styles.css has no content."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 Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0274". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Page Module:Citation/CS1/styles.css has no content.Weast, Robert C.; et al. (1978). CRC Handbook of Chemistry and Physics (59th ed.). West Palm Beach, FL: CRC Press. Template:ISBN.
  4. ^ a b Page Module:Citation/CS1/styles.css has no content."Ethyleneimine". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  5. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ a b c d Script error: No such module "Template wrapper".
  8. ^ Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Kanerva L, Keskinen H, Autio P, Estlander T, Tuppurainen M, Jolanki R (May 1995). "Occupational respiratory and skin sensitization caused by polyfunctional aziridine hardener". Clin Exp Allergy. 25 (5): 432–9. doi:10.1111/j.1365-2222.1995.tb01074.x. PMID 7553246. S2CID 28101810.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Sartorelli P, Pistolesi P, Cioni F, Napoli R, Sisinni AG, Bellussi L, Passali GC, Cherubini Di Simplicio E, Flori L (2003). "Skin and respiratory allergic disease caused by polyfunctional aziridine". Med Lav. 94 (3): 285–95. PMID 12918320.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Mapp CE (2001). "Agents, old and new, causing occupational asthma". Occup. Environ. Med. 58 (5): 354–60. doi:10.1136/oem.58.5.354. PMC 1740131. PMID 11303086.

Page Module:Side box/styles.css has no content.Page Template:Sister project/styles.css has no content.

Page Template:Plainlist/styles.css has no content.
Script error: No such module "Sister project logo".
Wikimedia Commons has media related to [[commons:Template:If then show|Template:If then show]].
Retrieved from "https://cosmopedia.co/index.php?title=Aziridine&oldid=1273466"