Allylamine

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title: "Allylamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["allylamines"] topic_path: "general/allylamines" source: "https://en.wikipedia.org/wiki/Allylamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477318190 | Name = Allylamine | ImageFile = Allylamine.png | ImageFile1 = Allylamine-3D-balls.png | ImageSize = 150 | ImageName = | PIN = Prop-2-en-1-amine | OtherNames = 2-Propen-1-amine 2-Propenamine Allyl amine 3-Amino-prop-1-ene 3-Aminopropene 3-Aminopropylene Monoallylamine |Section1={{Chembox Identifiers | UNII_Ref = | UNII = 48G762T011 | SMILES = C=CCN | InChI = 1/C3H7N/c1-2-3-4/h2H,1,3-4H2 | InChIKey = VVJKKWFAADXIJK-UHFFFAOYAW | StdInChI_Ref = | StdInChI = 1S/C3H7N/c1-2-3-4/h2H,1,3-4H2 | StdInChIKey_Ref = | StdInChIKey = VVJKKWFAADXIJK-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 107-11-9 | ChEMBL_Ref = | ChEMBL = 57286 | RTECS = BA5425000 | PubChem = 7853 | ChemSpiderID_Ref = | ChemSpiderID = 13835977 | EC_number = 203-463-9 | UNNumber = 2334 |Section2={{Chembox Properties | C=3|H=7|N=1 | Appearance = Colorless liquid | Density = 0.7630 g/cm3, liquid | Solubility = | MeltingPtC = -88 | BoilingPtC = 55 to 58 | pKa = 9.49 (conjugate acid; H2O) | Viscosity = |Section3={{Chembox Structure | MolShape = | Coordination = | CrystalStruct = | Dipole = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = Lachrymatory | NFPA-H = 4 | NFPA-F = 3 | NFPA-R = | FlashPtC = -28 | AutoignitionPtC = 374 | ExploLimits = 2-22% | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | LD50 = 106 mg/kg |Section8={{Chembox Related | OtherFunction_label = amine | OtherFunction = Propylamine | OtherCompounds = Allyl alcohol

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. Or by the reaction of allyl chloride with hexamine. Pure samples can be prepared by hydrolysis of allyl isothiocyanate. It behaves as a typical amine.

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

Other allylamines

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. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/fc/Allylamines.svg" caption="[[Flunarizine]] and [[naftifine]] are pharmacologically active allylamines."] ::

Safety

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

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society.
  3. Ludger Krähling. (2002). "Allyl Compounds". Wiley-VCH.
  4. "Synthesis of allylamine in ethanol".
  5. M. T. Leffler. (1938). "Allylamine". Organic Syntheses.
  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.. (1 January 2013). "Palladium catalyzed intermolecular hydroamination of 1-substituted allenes: an atom-economical method for the synthesis of N-allylamines". RSC Advances.

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allylamines