Allylamine

Summary

Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.

Allylamine
Allylamine.png
Allylamine-3D-balls.png
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
  • 107-11-9 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL57286 checkY
ChemSpider
  • 13835977 checkY
ECHA InfoCard 100.003.150 Edit this at Wikidata
EC Number
  • 203-463-9
  • 7853
RTECS number
  • BA5425000
UNII
  • 48G762T011 checkY
UN number 2334
  • DTXSID8024440 Edit this at Wikidata
  • 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 (conjugate acid; H2O)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Lachrymatory
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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)
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 ?)
Infobox references

Production and reactionsEdit

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]

Other allylaminesEdit

Diallylamine is a precursor to industrial products. Functionalized allylamines have 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.[7]

 
Flunarizine and naftifine are pharmacologically active allylamines.

SafetyEdit

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

ReferencesEdit

  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. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  3. ^ 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.
  4. ^ "Synthesis of allylamine in ethanol". ResearchGate. Retrieved 2020-06-30.
  5. ^ M. T. Leffler (1938). "Allylamine". Organic Syntheses. 18: 5. doi:10.15227/orgsyn.018.0005.
  6. ^ 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
  7. ^ 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.

External linksEdit