2-Picolylamine

2-Picolylamine can be prepared by the following reactions: (1) Hydrocarbonation reaction In a 250 ml three-necked flask, add 11.8 g (0.084 mol) of dried hexamethylenetetramine, 100 ml of acetonitrile, and 13.7 g (90.2%, 0.076 mol) of 2-chloromethylpyridine. Stir magnetically and reflux for 8 hours. Cool to room temperature and filter to obtain a white solid. (2) Hydrolysis reaction Add the white solid obtained in the previous step to a 250 ml three-necked flask, add 34 ml of hydrochloric acid, add 100 ml of methanol while stirring, reflux at 61 °C for 2 hours and then raise the temperature to 100 °C. Cool naturally to room temperature and add 40 ml of chloroform. Add 25% NaOH aqueous solution dropwise while stirring to adjust the pH to 8~9, separate the layers, extract the aqueous layer once with chloroform, and combine the chloroform layers. Chloroform was removed under reduced pressure, yielding a yellow liquid. Upon refrigeration, it solidified into a crude 2-Picolylamine. Recrystallization from methanol yielded white crystals of 2-Picolylamine.

It is usually used as the intermediate or raw material in the organic synthesis and pharmaceutical synthesis. For example, this chemical can promote the Al(OTf)3-catalyzed aminolysis of 1,2-epoxides to produce β-Amino alcohols N-2'-pyridylmethyl in excellent yields.¹ Moreover, this substance may function as the raw material to produce copper(Ⅱ) complexes with sulfonamides that act as the active chemical nucleases.² In addition, by using this chemical as substrate, an efficient [2+3] cycloaddition approach has been developed for the synthesis of pyridyl-appended fullerene ligands.³ Besides, 2-picolylamine is chosen as the recognition group to get better selectivity for a rhodamine-based “turn-on” fluorescent probe for Fe3+ in aqueous solution.⁴

1. Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L., Solvent-free Al(OTf)(3)-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: A key step in the synthesis of ionic liquids. J. Org. Chem. 2004, 69, 7745-7747.
2. Macias, B.; Villa, M. V.; Salgado, M.; Borras, J.; Gonzalez-Alvarez, M.; Sanz, F., Copper(II) complexes with sulfonamides derived from 2-picolylamine and their use as chemical nucleases. Inorg. Chim. Acta 2006, 359, 1465-1472.
3. Troshin, P. A.; Peregudov, A. S.; Muhlbacher, D.; Lyubovskaya, R. N., An efficient 2+3 cycloaddition approach to the synthesis of pyridyl-appended fullerene ligands. Eur. J. Org. Chem. 2005, 3064-3074.
4. Ji, S. Z.; Meng, X. M.; Ye, W. P.; Feng, Y.; Sheng, H. T.; Cai, Y. L.; Liu, J. S.; Zhu, X. F.; Guo, Q. X., A rhodamine-based "turn-on" fluorescent probe for Fe3+ in aqueous solution. Dalton Trans. 2014, 43, 1583-1588.

clear colorless to yellow or orange liquid

2-Picolylamine may be used as a derivatization agent to enhance the sensitivity of carboxylic acids and short-chain fatty acids for their determination in biological samples by liquid chromatography coupled to electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) and ultra-high performance liquid chromatography (UHPLC), respectively.

2-Picolylamine is a bihaptic amine that can be used:

• As a key precursor to synthesize various ionic liquids through the formation of β-amino alcohols as intermediates.
• As a chelating ligand for the synthesis of complexes such as zinc picolylamine complex and Cu(II) picolylamine complex.
• To functionalize poly(styrene-co-maleic anhydride) (PSMA) resin to facilitate the adsorption of uranium from aqueous solution.

ChEBI: 2-Pyridinemethanamine is a member of pyridines.

2-Picolylamine, a bihaptic nucleophile, is a bidentate ligand that is generally utilized for the preparation of various multidentate ligands and the corresponding complexes.

The initial threshold screening level (ITSL) for 2-(aminomethyl)pyridine is 0.1μg/m3 (annual averaging time).