Allylamine
Chemical compound From Wikipedia, the free encyclopedia
Chemical compound From Wikipedia, the free encyclopedia
Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.
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| Names | |
|---|---|
| Preferred IUPAC name
Prop-2-en-1-amine[1] | |
| Other names
2-Propen-1-amine 2-Propenamine Allyl amine 3-Amino-prop-1-ene 3-Aminopropene 3-Aminopropylene Monoallylamine | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.150 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 2334 |
CompTox Dashboard (EPA) |
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| Properties | |
| C3H7N | |
| Molar mass | 57.096 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.7630 g/cm3, liquid |
| Melting point | −88 °C (−126 °F; 185 K) |
| Boiling point | 55 to 58 °C (131 to 136 °F; 328 to 331 K) |
| Acidity (pKa) | 9.49 (conjugate acid; H2O)[2] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Lachrymatory |
| GHS labelling: | |
     | |
| Danger | |
| H225, H301, H310, H315, H319, H330, H335, H371, H373, H411 | |
| P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | −28 °C (−18 °F; 245 K) |
| 374 °C (705 °F; 647 K) | |
| Explosive limits | 2-22% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
106 mg/kg |
| Related compounds | |
Related amine |
Propylamine |
Related compounds |
Allyl alcohol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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]
Allylamine, like other allyl derivatives is a lachrymator and skin irritant. Its oral LD50 is 106 mg/kg for rats.
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