Allylamine

Allylamine
IUPAC name 3-Amino-prop-1-ene
Other names 3-Aminopropene; 3-Aminopropylene; Monoallylamine; 2-Propenamine; 2-Propen-1-amine; Allyl amine
Identifiers
CAS number	107-11-9 Y
ChemSpider	13835977 Y
UNII	48G762T011 Y
ChEMBL	CHEMBL57286 Y
RTECS number	BA5425000
Jmol-3D images	Image 1
SMILES C=CCN
InChI InChI=1S/C3H7N/c1-2-3-4/h2H,1,3-4H2 Y Key: VVJKKWFAADXIJK-UHFFFAOYSA-N Y InChI=1/C3H7N/c1-2-3-4/h2H,1,3-4H2 Key: VVJKKWFAADXIJK-UHFFFAOYAW
Properties
Molecular formula	C3H7N
Molar mass	57.09 g mol−1
Appearance	Colorless liquid
Density	0.7630 g/cm3, liquid
Melting point	-88 °C, 185 K, -126 °F
Boiling point	55-58 °C, 328-331 K, 131-136 °F
Acidity (pKa)	9.49[1]
Hazards
R-phrases	R11 R23/24/25 R51/53
S-phrases	S9 S16 S24/25 S45 S61
Main hazards	Lachrymatory
NFPA 704	3 4 0
Flash point	-28 °C
Related compounds
Related amine	Propylamine
Related compounds	Allyl alcohol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Allylamine is an organic compound with the formula C₃H₅NH₂. This colorless liquid is the simplest stable unsaturated amine.

Production

All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chloride with ammonia followed by distillation.^[2] Pure samples can be prepared by hydrolysis of allyl isothiocyanate.^[3] It behaves as a typical amine.^[4]

Reactions

Polymerization can be used to prepare the homopolymer (poly(allylamine)) or copolymers. The polymers are promising membranes for use in reverse osmosis.^[2]

Safety

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

References

1. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
2. ^ ^{a b} Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche "Allyl Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a01_425
3. ^ M. T. Leffler (1943), "Allylamine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0024 ; Coll. Vol. 2: 24 
4. ^ 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