Tris((1-benzyl-4-triazolyl)methyl)amine (TBTA) is a tertiary amine containing the 1,2,3-triazole moiety. When used as a ligand, complexed to copper(I), it allows for quantitative, regioselective formal Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic solvents.
It is believed that the ligand promotes catalysis through the stabilization of the copper(I)-oxidation state, while still allowing for the catalytic cycle of the CuAAC reaction to proceed.
Single crystal X-ray diffraction of the Cu(I) complex of tris((1-benzyl-4-triazolyl)methyl)amine revealed an unusual dinuclear dication with one triazole unit bridging two metal centers, and is an effective catalyst for the 'click' cycloaddition reaction. The structure of the complex of TBTA with Cu(II) in the crystalline state is trigonal bipyramidal and can be reduced to the active 'click' catalyst form by sodium ascorbate, copper metal, or other reducing agents.
In the literature, it has been gaining widespread use as a biochemical tool for the tagging of proteins and enzymes. The compound is now commercially available through Sigma-Aldrich and Invitrogen. It may be prepared by the click reaction between tripropargylamine and benzyl azide:[1][2]
Referencesedit
^Timothy R. Chan; Robert Hilgraf; K. Barry Sharpless & Valery V. Fokin (2004). "Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis". Org. Lett.6 (17): 2853–2855. doi:10.1021/ol0493094. PMID 15330631.
tris, benzyltriazolylmethyl, amine, tris, benzyl, triazolyl, methyl, amine, tbta, tertiary, amine, containing, triazole, moiety, when, used, ligand, complexed, copper, allows, quantitative, regioselective, formal, huisgen, dipolar, cycloadditions, between, alk. Tris 1 benzyl 4 triazolyl methyl amine TBTA is a tertiary amine containing the 1 2 3 triazole moiety When used as a ligand complexed to copper I it allows for quantitative regioselective formal Huisgen 1 3 dipolar cycloadditions between alkynes and azides in a variety of aqueous and organic solvents Tris benzyltriazolylmethyl amine NamesPreferred IUPAC name 1 1 Benzyl 1H 1 2 3 triazol 4 yl N N bis 1 benzyl 1H 1 2 3 triazol 4 yl methyl methanamineIdentifiersCAS Number 510758 28 8 Y3D model JSmol Interactive imageChemSpider 9378431 YECHA InfoCard 100 221 401PubChem CID 11203363UNII TC4DSF6TA2 YCompTox Dashboard EPA DTXSID20458589InChI InChI 1S C30H30N10 c1 4 10 25 11 5 1 16 38 22 28 31 34 38 19 37 20 29 23 39 35 32 29 17 26 12 6 2 7 13 26 21 30 24 40 36 33 30 18 27 14 8 3 9 15 27 h1 15 22 24H 16 21H2Key WKGZJBVXZWCZQC UHFFFAOYSA N YInChI 1S C30H30N10 c1 4 10 25 11 5 1 16 38 22 28 31 34 38 19 37 20 29 23 39 35 32 29 17 26 12 6 2 7 13 26 21 30 24 40 36 33 30 18 27 14 8 3 9 15 27 h1 15 22 24H 16 21H2InChI 1S C30H30N10 c1 4 10 25 11 5 1 16 38 22 28 31 34 38 19 37 20 29 23 39 35 32 29 17 26 12 6 2 7 13 26 21 30 24 40 36 33 30 18 27 14 8 3 9 15 27 h1 15 22 24H 16 21H2Key WKGZJBVXZWCZQC UHFFFAOYSA NSMILES c1ccc cc1 Cn2cc nn2 CN Cc3cn nn3 Cc4ccccc4 Cc5cn nn5 Cc6ccccc6PropertiesChemical formula C 30H 30N 10Molar mass 530 640 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references It is believed that the ligand promotes catalysis through the stabilization of the copper I oxidation state while still allowing for the catalytic cycle of the CuAAC reaction to proceed Single crystal X ray diffraction of the Cu I complex of tris 1 benzyl 4 triazolyl methyl amine revealed an unusual dinuclear dication with one triazole unit bridging two metal centers and is an effective catalyst for the click cycloaddition reaction The structure of the complex of TBTA with Cu II in the crystalline state is trigonal bipyramidal and can be reduced to the active click catalyst form by sodium ascorbate copper metal or other reducing agents In the literature it has been gaining widespread use as a biochemical tool for the tagging of proteins and enzymes The compound is now commercially available through Sigma Aldrich and Invitrogen It may be prepared by the click reaction between tripropargylamine and benzyl azide 1 2 References edit Timothy R Chan Robert Hilgraf K Barry Sharpless amp Valery V Fokin 2004 Polytriazoles as Copper I Stabilizing Ligands in Catalysis Org Lett 6 17 2853 2855 doi 10 1021 ol0493094 PMID 15330631 Donnelly P S Zanatta S D Zammit S C White J M Williams S J 2008 Click Cycloaddition Catalysts Copper I and Copper II Tris triazolylmethyl amine Complexes Chem Commun 21 2459 2461 doi 10 1039 b719724a PMID 18491014 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Retrieved from https en wikipedia org w index php title Tris benzyltriazolylmethyl amine amp oldid 1105840472, wikipedia, wiki, book, books, library,
