Allylamine
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| UN number | 2334 |
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| Appearance | Colorless liquid |
| Density | 0.7630 g/cm3, liquid |
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| Acidity (pKa) | 9.49 (conjugate acid; H2O)[2] |
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| Explosive limits | 2-22% |
| Template:Longitem | Propylamine |
| Template:Longitem | Allyl alcohol |
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Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.
Production and reactions
All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chloride with ammonia followed by distillation.[3] Or by the reaction of allyl chloride with hexamine.[4] Pure samples can be prepared by hydrolysis of allyl isothiocyanate.[5] It behaves as a typical amine.[6]
Polymerization can be used to prepare the homopolymer (polyallylamine) or copolymers. The polymers are promising membranes for use in reverse osmosis.[3]
Other allylamines
Diallylamine is a precursor to industrial products. Functionalized allylamines have pharmaceutical applications. Pharmaceutically important allylamines include flunarizine and naftifine; the latter spurred the development of Petasis' borono-Mannich reaction. Flunarizine aids in the relief of migraines while naftifine acts to fight common fungus causing infections such as athlete's foot, jock itch, and ringworm.[7]
Safety
Allylamine, like other allyl derivatives is a lachrymator and skin irritant. Its oral LD50 is 106 mg/kg for rats.
References
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- ↑ Henk de Koning, W. Nico Speckamp "Allylamine" in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, Weinheim. Script error: No such module "CS1 identifiers". Article Online Posting Date: April 15, 2001
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External links
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