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词条 Allylamine
释义

  1. Production and reactions

  2. Other allylamines

  3. Safety

  4. References

  5. External links

{{chembox
| Watchedfields = changed
| verifiedrevid = 477318190
| Name = Allylamine
| ImageFile = Allylamine.png
| ImageFile1 = Allylamine-3D-balls.png
| ImageSize = 150
| ImageName =
| PIN = Prop-2-en-1-amine[1]
| OtherNames = 2-Propen-1-amine
2-Propenamine
Allyl amine
3-Amino-prop-1-ene
3-Aminopropene
3-Aminopropylene
Monoallylamine
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 48G762T011
| SMILES = C=CCN
| InChI = 1/C3H7N/c1-2-3-4/h2H,1,3-4H2
| InChIKey = VVJKKWFAADXIJK-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H7N/c1-2-3-4/h2H,1,3-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VVJKKWFAADXIJK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 107-11-9
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 57286
| RTECS = BA5425000
| PubChem = 7853
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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)[2]
| 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 = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|301|310|315|319|330|335|371|373|401|411}}
| 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}}
| 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.[3] Pure samples can be prepared by hydrolysis of allyl isothiocyanate.[4] It behaves as a typical amine.[5]

Polymerization can be used to prepare the homopolymer (polyallylamine) or copolymers. The polymers are promising membranes for use in reverse osmosis.[3]

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.[6]

Safety

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

References

1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 681 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}
2. ^{{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}}
3. ^{{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}}
4. ^{{OrgSynth | author = M. T. Leffler | title = Allylamine | collvol = 2 | collvolpages = 24 | year = 1943 | prep = CV2P0024}}
5. ^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
6. ^{{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}}

External links

  • {{PubChem|2=Allylamine}} at National Center for Biotechnology Information
{{Authority control}}

2 : Amines|Allyl compounds

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