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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Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
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Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
Organogermanium(II) Hydrides as a Source of Highly Soluble LiH
Deraet, Xavier,Dostál, Libor,Jambor, Roman,R??i?ka, Ale?,Tremmel, Jakub,Turek, Jan,Tydlitát, Ji?í
supporting information, (2020/05/08)
The reactions of monomeric C,N-chelated organogermanium(II) hydride L(H)Ge?BH3 with organolithium salts RLi yielded lithium hydrogermanatoborates (Li(THF)2{BH3[L(H)GeR]})2. Compound (Li(THF)2{BH3[L(H)GePh]})2 was used as a source of LiH for the reduction of organic C=O or C=N bonds in nonpolar solvents accompanied by the elimination of a neutral complex L(Ph)Ge?BH3. The interaction of (Li(THF)2{BH3[L(H)GePh]})2 with the polar C=O bond was further investigated by computational studies revealing a plausible geometry of a pre-reactive intermediate. The experimental and theoretical studies suggest that, although the Li atom of (Li(THF)2{BH3[L(H)GePh]})2 coordinates the C=O bond, the GeH fragment is the active species in the reduction reaction. Finally, benzaldehyde was reduced by a mixture of L(H)Ge?BH3 with PhLi in nonpolar solvents.