3731-51-9 Usage
Description
2-Picolylamine, a bihaptic nucleophile, is a bidentate ligand that is generally utilized for the preparation of various multidentate ligands and the corresponding complexes. It is usually used as the intermediate or raw material in the organic synthesis and pharmaceutical synthesis. 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. Moreover, this substance may function as the raw material to produce copper(Ⅱ) complexes with sulfonamides that act as the active chemical nucleases. In addition, by using this chemical as a substrate, an efficient [2+3] cycloaddition approach has been developed for the synthesis of pyridyl-appended fullerene ligands. 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. It is a clear colorless to yellow or orange liquid.
Uses
Used in Ionic Liquid Synthesis:
2-Picolylamine is used as a key precursor for the synthesis of various ionic liquids through the formation of β-amino alcohols as intermediates. This application is significant in the development of novel ionic liquids with tailored properties for diverse applications.
Used in Complex Synthesis:
2-Picolylamine is used as a chelating ligand for the synthesis of complexes such as zinc picolylamine complex and Cu(II) picolylamine complex. These complexes find applications in various fields, including catalysis and pharmaceuticals.
Used in Nuclear Industry:
2-Picolylamine is used to functionalize poly(styrene-co-maleic anhydride) (PSMA) resin to facilitate the adsorption of uranium from aqueous solutions. This application is crucial for the nuclear industry, where the efficient removal of uranium from wastewater is essential.
Used in Analytical Chemistry:
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. This application improves the accuracy and reliability of analytical methods in various research and diagnostic fields.
Reference
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.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3731-51-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,7,3 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3731-51:
(6*3)+(5*7)+(4*3)+(3*1)+(2*5)+(1*1)=79
79 % 10 = 9
So 3731-51-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2/c7-5-6-3-1-2-4-8-6/h1-4H,5,7H2/p+1
3731-51-9Relevant articles and documents
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Irving,da Silva
, p. 945,948 (1963)
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Nickel(II)-Promoted Ethanolysis and Hydrolysis of N-(2-pyridylmethyl)urea. A model for Urease
Blakeley, Robert L.,Treston, Anthony,Andrews, Robert K.,Zerner, Burt
, p. 612 - 614 (1982)
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Direct Conversion of Hydrazones to Amines using Transaminases
Carter, Eve M.,Hailes, Helen C.,Sheppard, Tom D.,Subrizi, Fabiana,Ward, John M.
, p. 4520 - 4523 (2021/09/20)
Transaminase enzymes (TAms) have been widely used for the amination of aldehydes and ketones, often resulting in optically pure products. In this work, transaminases were directly reacted with hydrazones in a novel approach to form amine products. Several substrates were investigated, including those with furan and phenyl moieties. It was determined that the amine yields increased when an additional electrophile was added to the reaction mixture, suggesting that they can sequester the hydrazine released in the reaction. Pyridoxal 5’-phosphate (PLP), a cofactor for transaminases, and polyethylene glycol (PEG)-aldehydes were both found to increase the yield of amine formed. Notably, the amination of (S)-(?)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazones gave promising results as a method to form chiral β-substituted amines in good yield.
A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation
Formenti, Dario,Mocci, Rita,Atia, Hanan,Dastgir, Sarim,Anwar, Muhammad,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
supporting information, p. 15589 - 15595 (2020/10/02)
Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.