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Revision as of 14:28, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 454314972 of page Tris-(Benzyltriazolylmethyl)amine for the Chem/Drugbox validation project (updated: 'StdInChI').  Latest revision as of 02:00, 22 August 2022 edit Fswitzer4 (talk | contribs)Extended confirmed users10,572 editsm Added UNII 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| verifiedrevid = 470617490
| ImageFile = Tris-(benzyltriazolylmethyl)amine.png | ImageFile = Tris(benzyltriazolylmethyl)amine.png
| ImageSize =
| ImageAlt = Skeletal formula of TBTA
⚫ | IUPACName = 1-(1-benzyltriazol-4-yl)-N,N-bismethanamine
| ImageFile1 = Tris(benzyltriazolylmethyl)amine-3D-balls.png
| ImageSize1 = 230
| ImageAlt1 = Ball-and-stick model of the TBTA molecule
⚫ | PIN = 1-(1-Benzyl-1''H''-1,2,3-triazol-4-yl)-''N'',''N''-bismethanamine
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| 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,16-21H2 | 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,16-21H2
| InChIKey1 = WKGZJBVXZWCZQC-UHFFFAOYSA-N | InChIKey1 = WKGZJBVXZWCZQC-UHFFFAOYSA-N
| InChI1 = 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,16-21H2 | InChI1 = 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,16-21H2
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =
| PubChem = 11203363 | CASNo = 510758-28-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | ChemSpiderID = 9378431
| UNII = TC4DSF6TA2
⚫ | StdInChIKey = WKGZJBVXZWCZQC-UHFFFAOYSA-N
| PubChem = 11203363
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 9378431
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = WKGZJBVXZWCZQC-UHFFFAOYSA-N
| SMILES = c1ccc(cc1)Cn2cc(nn2)CN(Cc3cn(nn3)Cc4ccccc4)Cc5cn(nn5)Cc6ccccc6 | SMILES = c1ccc(cc1)Cn2cc(nn2)CN(Cc3cn(nn3)Cc4ccccc4)Cc5cn(nn5)Cc6ccccc6
| StdInChI = 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,16-21H2 | StdInChI = 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,16-21H2
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 30 | H = 30 | N = 10 | C=30 | H=30 | N=10
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Tris((1-benzyl-4-triazolyl)methyl)amine''' (TBTA) is a tertiary ] containing the ] moiety. When used as a ligand, complexed to copper(I), it allows for quantitative, regioselective formal ]s between ]s and ]s, 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 ] and ]:<ref name = chan>{{cite journal |author1=Timothy R. Chan |author2=Robert Hilgraf |author3=K. Barry Sharpless |author4=Valery V. Fokin |name-list-style=amp | journal = ] | year = 2004 | volume = 6 | issue = 17 | pages = 2853–2855 | doi = 10.1021/ol0493094 | title = Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis | pmid=15330631}}</ref><ref>{{cite journal | author = Donnelly, P.S., Zanatta, S.D., Zammit, S.C., White, J.M., Williams, S.J. | journal = ] | year = 2008 | pages = 2459–2461 | doi = 10.1039/b719724a | title = '"Click" Cycloaddition Catalysts: Copper(I) and Copper(II) Tris(triazolylmethyl)amine Complexes' | issue = 21| pmid = 18491014 }}</ref>

:]

==References==
{{Reflist}}

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