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Allylamine

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Allylamine
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 Edit this at Wikidata
RTECS number
  • BA5425000
UNII
  • InChI=1S/C3H7N/c1-2-3-4/h2H,1,3-4H2 checkY
    Key: VVJKKWFAADXIJK-UHFFFAOYSA-N checkY
  • InChI=1/C3H7N/c1-2-3-4/h2H,1,3-4H2
    Key: VVJKKWFAADXIJK-UHFFFAOYAW
  • C=CCN
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[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Lachrymatory
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 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. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
4
3
Flash point −28 °C (−18 °F; 245 K)
374 °C (705 °F; 647 K)
Explosive limits 2-22%
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)

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.[3] Pure samples can be prepared by hydrolysis of allyl isothiocyanate.[4] It behaves as a typical amine.[5]

Polymerization can be used to prepare the homopolymer (polyallylamine) or copolymers. The polymers are promising membranes for use in reverse osmosis.[3]

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.[6]

Flunarizine and naftifine are pharmacologically 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. ^ 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.
  2. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  3. ^ 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
  4. ^ M. T. Leffler (1943). "Allylamine". Organic Syntheses; Collected Volumes, vol. 2, p. 24.
  5. ^ 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
  6. ^ 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.
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