Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.
| |
| |
| 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)
|
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.150 |
| EC Number |
|
PubChem CID
|
|
| RTECS number |
|
| UNII | |
| UN number | 2334 |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
| |
Production and reactions
editAll 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
editDiallylamine 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
editAllylamine, like other allyl derivatives is a lachrymator and skin irritant. Its oral LD50 is 106 mg/kg for rats.
References
edit- ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 681. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
- ^ a b Ludger Krähling; Jürgen Krey; Gerald Jakobson; Johann Grolig; Leopold Miksche (2002). "Allyl Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_425. ISBN 3527306730.
- ^ "Synthesis of allylamine in ethanol". ResearchGate. Retrieved 2020-06-30.
- ^ M. T. Leffler (1938). "Allylamine". Organic Syntheses. 18: 5. doi:10.15227/orgsyn.018.0005.
- ^ Henk de Koning, W. Nico Speckamp "Allylamine" in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, Weinheim. doi:10.1002/047084289X.ra043 Article Online Posting Date: April 15, 2001
- ^ Beck, John F.; Samblanet, Danielle C.; Schmidt, Joseph A. R. (1 January 2013). "Palladium catalyzed intermolecular hydroamination of 1-substituted allenes: an atom-economical method for the synthesis of N-allylamines". RSC Advances. 3 (43): 20708. Bibcode:2013RSCAd...320708B. doi:10.1039/c3ra43870h.