| Revision as of 05:21, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468569006 of page Allylamine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 22:24, 15 May 2024 edit 208.86.232.16 (talk) →Production and reactions |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 443376335 |
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| verifiedrevid = 477318190 |
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| Name = Allylamine |
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| Name = Allylamine |
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| ImageFile = Allylamine.png |
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| ImageFile = Allylamine.png |
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| ImageSize = 150 |
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| ImageSize = 150 |
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| ImageName = |
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| ImageName = |
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| PIN = Prop-2-en-1-amine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 681 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| IUPACName = 3-Amino-prop-1-ene |
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| OtherNames = 3-Aminopropene; 3-Aminopropylene; Monoallylamine; 2-Propenamine; 2-Propen-1-amine; Allyl amine |
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| OtherNames = 2-Propen-1-amine<br />2-Propenamine<br />Allyl amine<br />3-Amino-prop-1-ene<br />3-Aminopropene<br />3-Aminopropylene<br />Monoallylamine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 48G762T011 |
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| UNII = 48G762T011 |
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| ChEMBL = 57286 |
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| ChEMBL = 57286 |
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| RTECS = BA5425000 |
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| RTECS = BA5425000 |
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| PubChem = 7853 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13835977 |
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| ChemSpiderID = 13835977 |
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| EC_number = 203-463-9 |
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| UNNumber = 2334 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3|H=7|N=1 |
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| C=3|H=7|N=1 |
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| Appearance = Colorless liquid |
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| Appearance = Colorless liquid |
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| Density = 0.7630 g/cm<sup>3</sup>, liquid |
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| Density = 0.7630 g/cm<sup>3</sup>, liquid |
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| Solubility = |
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| Solubility = |
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| MeltingPtC = -88 |
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| MeltingPtC = -88 |
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| BoilingPtCL = 55 |
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| BoilingPtC = 55 to 58 |
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| pKa = 9.49 (conjugate acid; H<sub>2</sub>O)<ref>{{cite journal |last1=Hall |first1=H. K. |title=Correlation of the Base Strengths of Amines |journal=Journal of the American Chemical Society |date=1957 |volume=79 |issue=20 |pages=5441–5444 |doi=10.1021/ja01577a030}}</ref> |
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| BoilingPtCH = 58 |
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| Viscosity = |
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| pKa = 9.49<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref> |
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| Viscosity = |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| MolShape = |
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| Coordination = |
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| Coordination = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Lachrymatory |
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| MainHazards = Lachrymatory |
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| NFPA-H = 4 |
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| NFPA-H = 4 |
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| NFPA-F = 3 |
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| NFPA-F = 3 |
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| NFPA-R = |
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| NFPA-R = |
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| FlashPt = -28 °C |
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| FlashPtC = -28 |
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| AutoignitionPtC = 374 |
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| RPhrases = {{R11}} {{R23/24/25}} {{R51/53}} |
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| ExploLimits = 2-22% |
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| SPhrases = {{S9}} {{S16}} {{S24/25}} {{S45}} {{S61}} |
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| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|225|301|310|315|319|330|335|371|373|411}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|262|264|270|271|273|280|284|301+310|302+350|302+352|303+361+353|304+340|305+351+338|309+311|310|312|314|320|321|322|330|332+313|337+313|361|362|363|370+378|391|403+233|403+235|405|501}} |
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| LD50 = 106 mg/kg |
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| Section8 = {{Chembox Related |
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| Function = ] |
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| OtherFunction_label = ] |
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| OtherFunctn = ] |
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| OtherFunction = ] |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Allylamine''' is an ] with the formula C<sub>3</sub>H<sub>5</sub>NH<sub>2</sub>. This colorless liquid is the simplest stable ] ]. |
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==Production and reactions== |
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All three allylamines, mono-, di-, and ], are produced by the treating ] with ] followed by distillation.<ref name=Ullmann>{{cite encyclopedia|author=Ludger Krähling|author2=Jürgen Krey|author3=Gerald Jakobson|author4=Johann Grolig|author5=Leopold Miksche|title=Allyl Compounds|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a01_425|isbn=3527306730}}</ref> Or by the reaction of allyl chloride with ].<ref>{{Cite web|title=Synthesis of allylamine in ethanol|url=https://www.researchgate.net/publication/288677473|access-date=2020-06-30|website=ResearchGate|language=en}}</ref> Pure samples can be prepared by hydrolysis of ].<ref>{{cite journal|journal=Organic Syntheses | author = M. T. Leffler | title = Allylamine | volume = 18 | page = 5 | year = 1938 | doi = 10.15227/orgsyn.018.0005}}</ref> It behaves as a typical amine.<ref>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</ref> |
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Polymerization can be used to prepare the homopolymer (]) or copolymers. The polymers are promising membranes for use in ].<ref name=Ullmann/> |
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==Other allylamines== |
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] is a precursor to industrial products. Functionalized allylamines have pharmaceutical applications. Pharmaceutically important allylamines include ] and ]; the latter spurred the development of ]. Flunarizine aids in the relief of migraines while naftifine acts to fight common ] causing infections such as ], ], and ].<ref name="Beck 20708">{{cite journal|last=Beck|first=John F.|author2=Samblanet, Danielle C.|author3= Schmidt, Joseph A. R.|title=Palladium catalyzed intermolecular hydroamination of 1-substituted allenes: an atom-economical method for the synthesis of N-allylamines|journal=RSC Advances|date=1 January 2013|volume=3|issue=43|pages=20708|doi=10.1039/c3ra43870h|bibcode=2013RSCAd...320708B}}</ref> |
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] and ] are pharmacologically active allylamines.]] |
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==Safety== |
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Allylamine, like other allyl derivatives is a ] and skin irritant. Its oral {{LD50}} is 106 mg/kg for rats. |
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==References== |
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{{reflist}} |
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==External links== |
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* {{PubChem|2=Allylamine}} at ] |
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{{Authority control}} |
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] |