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Title: Allylamine  
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Subject: WikiProject Outlines/Drafts/Outline of tinea, List of MeSH codes (D02), Highly hazardous chemical, List of UN numbers 2301 to 2400, Amines
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IUPAC name
Other names
3-Aminopropene; 3-Aminopropylene; Monoallylamine; 2-Propenamine; 2-Propen-1-amine; Allyl amine
ChemSpider  Y
Jmol-3D images Image
RTECS number BA5425000
Molar mass 57.10 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[1]
Main hazards Lachrymatory
R-phrases R51/53
S-phrases S9 S16 S24/25 S45 S61
NFPA 704
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
Related compounds
Allyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Allylamine is an unsaturated amine.


  • Production and reactions 1
  • Other allylamines 2
  • Safety 3
  • References 4
  • External links 5

Production and reactions

All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chloride with ammonia followed by distillation.[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.[2]

Other allylamines

Functionalized allylamines have extensive pharmaceutical applications. Pharmaceutically important allylamines include flunarizine and naftifine. 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]

Flunarizine and naftifine are pharmaceutically active allylamines.


Allylamine, like other allyl derivatives is a lachrymator and skin irritant. Its oral LD50 is 106 mg/kg for rats.


  1. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  2. ^ a b Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche "Allyl Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_425
  3. ^ M. T. Leffler (1943). "Allylamine".  
  4. ^ 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
  5. ^ 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.  

External links

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