Allylamine

Allylamine
Names
	Preferred IUPAC name Prop-2-en-1-amine
	Other names 2-Propen-1-amine; 2-Propenamine; Allyl amine; 3-Amino-prop-1-ene; 3-Aminopropene; 3-Aminopropylene; Monoallylamine
Identifiers
CAS Number	107-11-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL57286 ;
ChemSpider	13835977 ;
ECHA InfoCard	100.003.150
EC Number	203-463-9;
PubChem CID	7853;
RTECS number	BA5425000;
UNII	48G762T011 ;
UN number	2334
CompTox Dashboard (EPA)	DTXSID8024440 ;
	InChI InChI=1S/C3H7N/c1-2-3-4/h2H,1,3-4H2 Key: VVJKKWFAADXIJK-UHFFFAOYSA-N ; InChI=1/C3H7N/c1-2-3-4/h2H,1,3-4H2 Key: VVJKKWFAADXIJK-UHFFFAOYAW;
	SMILES C=CCN;
Properties
Chemical formula	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)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Lachrymatory
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H310, H315, H319, H330, H335, H371, H373, H411
Precautionary statements	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)	4 3
Flash point	−28 °C (−18 °F; 245 K)
Autoignition; temperature	374 °C (705 °F; 647 K)
Explosive limits	2-22%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) 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.^[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

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

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

References

^ 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.
^ 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.
^ ^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.
^ "Synthesis of allylamine in ethanol". ResearchGate. Retrieved 2020-06-30.
^ M. T. Leffler (1938). "Allylamine". Organic Syntheses. 18: 5. doi:10.15227/orgsyn.018.0005.
^ 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
^ 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.

External links

Allylamine from PubChem at National Center for Biotechnology Information

[iupac2013-1] 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.

[Ullmann-3] 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

[Beck_20708-7] 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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