Allylamine

Structural formula
General
Surname	Allylamine
other names	Prop-2-en-1-amine ( IUPAC ) Prop-2-enamine 3-aminopropene 3-aminopropylene 3-aminoprop-1-en 2-propenylamine
Molecular formula	C 3 H 7 N
Brief description	colorless to yellowish liquid with an ammonia-like odor
External identifiers / databases
CAS number 107-11-9 EC number 203-463-9 ECHA InfoCard 100.003.150 PubChem 7853 Wikidata Q417414
properties
Molar mass	57.09 g mol −1
Physical state	liquid
density	0.76 g cm −3
Melting point	−88 ° C
boiling point	53 ° C
Vapor pressure	262 h Pa (20 ° C)
solubility	miscible with water
Refractive index	1.4205 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-301-310-331-411 P: 210-261-273-280-301 + 310-302 + 350
Toxicological data	102 mg kg −1 ( LD 50 ,  rat ,  oral )
Thermodynamic properties
ΔH f 0	−10.0 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Allylamine , also known as 3-aminopropen , 3-aminopropylene or propen 1-3-amino- called, is a amino - derivative of propene .

properties

Allylamine is a highly flammable liquid that can be mixed with water. The aqueous solution has an alkaline reaction . The pH of a solution of 5.7 g in one liter of water is 11.2. The vapors of the highly volatile allylamine can form explosive mixtures with air. Allylamine, as well as some derivatives of this compound, are inhibitors of the bovine enzyme BPAO ( bovine plasma amine oxidase )

toxicity

Allylamine vapors, as well as liquid allylamine, are highly irritating to the eyes and skin. Allylamine is a cardiovascular toxin . The administration of allylamine in rats triggers Erdheim-Gsell's cystic median necrosis of the aorta and arteriosclerosis .

use

Allylamine is the basic monomer for the synthesis of polyallylamine (PAAm or PAH = polyallylamine hydrochloride). The polymerization can take place both free-radical and in plasma (plasma-assisted chemical vapor deposition ( PECVD )). Allylamine is a building block for the synthesis of terbinafine . and other fungicides from the class of the allylamines.

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on allylamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-12.
3. ↑ Entry on allylamines in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.
5. ↑ HB Jeon, LM Sayre: Highly potent propargylamine and allylamine inhibitors of bovine plasma amine oxidase. In: Biochem Biophys Res Commun . 304/2003, pp. 788-794; PMID 12727226 .
6. ↑ D. Kumar et al .: Allylamine and beta-aminopropionitrile induced aortic medial necrosis: mechanisms of synergism. In: Toxicology 125/1998, pp. 107-115; PMID 9570326 .
7. ↑ DJ Conklin, BJ Boor: Allylamine cardiovascular toxicity: evidence for aberrant vasoreactivity in rats. In: Toxicology and applied pharmacology 148/1998, pp. 245-251; PMID 9473532 .
8. ↑ A. Choukourov include: Mechanistic studies of plasma polymerization of allylamines. In: J Phys Chem B 109/2005, pp. 23086-23095; PMID 16854007 .
9. ↑ G. Petranyi et al: Antifungal activity of the allylamine derivative terbinafine in vitro. In: Antimicrobial Agents and Chemotherapy 31/1987, pp. 1365-1368; PMID 3674847 ; PMC 174943 (free full text).
10. ↑ NS Ryder: Specific inhibition of fungal sterol biosynthesis by SF 86-327, a new allylamine antimycotic agent. In: Antimicrob Agents Chemother 27/1985, pp. 252-256; PMID 4039119 ; PMC 176248 (free full text).
11. ↑ G. Petranyi et al: Allylamine derivatives: new class of synthetic antifungal agents inhibiting fungal squalene epoxidase. In: Science 224/1984, pp. 1239-1241; PMID 6547247 .
12. ^ I. Salmoiraghi et al.: Allylamine type xanthone antimycotics. In: Arch Pharm 331/1998, pp. 225-227. PMID 9713256 .

literature

• P. Nussbaumer, I. Leitner, K. Mraz, A. Stütz: Synthesis and structure-activity relationships of side-chain-substituted analogs of the allylamine antimycotic terbinafine lacking the central amino function. In: Journal of medicinal chemistry. Volume 38, Number 10, May 1995, pp. 1831-1836, PMID 7752208 .