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
EC Number
  • 203-463-9
RTECS number
  • BA5425000
UNII
UN number 2334
  • 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)
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).
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Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.

Production and reactions

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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 allylamines

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Diallylamine 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]

Flunarizine and naftifine are pharmacologically active allylamines.

Safety

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

References

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  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.
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