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Open Access Articles- Top Results for Allylamine

Allylamine

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Allylamine
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IUPAC name
3-Amino-prop-1-ene
Other names
3-Aminopropene; 3-Aminopropylene; Monoallylamine; 2-Propenamine; 2-Propen-1-amine; Allyl amine
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107-11-9 7pxY
ChEMBL ChEMBL57286 7pxY
ChemSpider 13835977 7pxY
Jmol-3D images Image
RTECS number BA5425000
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C3H7N
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance Colorless liquid
Density 0.7630 g/cm3, liquid
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Acidity (pKa) 9.49[1]
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Main hazards Lachrymatory
R-phrases R11 R23/24/25 R51/53
S-phrases S9 S16 S24/25 S45 S61
NFPA 704

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Explosive limits 2-22%
106 mg/kg
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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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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]

File:Allylamines.tif
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

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