Allylamine

Allylamine
Names
IUPAC name
3-Amino-prop-1-ene
Other names
3-Aminopropene; 3-Aminopropylene; Monoallylamine; 2-Propenamine; 2-Propen-1-amine; Allyl amine
Identifiers
107-11-9 Yes
ChEMBL ChEMBL57286 Yes
ChemSpider 13835977 Yes
Jmol-3D images Image
RTECS number BA5425000
UNII 48G762T011 Yes
Properties
Molecular formula
 C3H7N
Molar mass 57.09 g·mol−1
Appearance Colorless liquid
Density 0.7630 g/cm3, liquid
Melting point −88 °C (−126 °F; 185 K)
Boiling point 55 °C (131 °F; 328 K)
Acidity (pKa) 9.49[1]
Hazards
Main hazards Lachrymatory
R-phrases R11 R23/24/25 R51/53
S-phrases S9 S16 S24/25 S45 S61
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
3
4
Flash point −28 °C (−18 °F; 245 K)
374 °C (705 °F; 647 K)
Explosive limits 2-22%
106 mg/kg
Related compounds
Related amine
Propylamine
Related compounds
 Allyl alcohol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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.[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.

Safety

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

References

  1. ↑ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  2. ↑ 2.0 2.1 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". Org. Synth.; Coll. Vol. 2, p. 24
  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. doi:10.1039/c3ra43870h.

External links