Allylamine
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.[1] Or by the reaction of allyl chloride with hexamine.[2] Pure samples can be prepared by hydrolysis of allyl isothiocyanate.[3] It behaves as a typical amine.[4]
Polymerization can be used to prepare the homopolymer (polyallylamine) or copolymers. The polymers are promising membranes for use in reverse osmosis.[1]
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.[5]
Safety
Allylamine, like other allyl derivatives is a lachrymator and skin irritant. Its oral LD50 is 106 mg/kg for rats.
References
External links
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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 "doi". Article Online Posting Date: April 15, 2001
- ↑ Script error: No such module "Citation/CS1".