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Sigma-Aldrich

Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine

97%

Synonym(s):

TBTA

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About This Item

Empirical Formula (Hill Notation):
C30H30N10
CAS Number:
Molecular Weight:
530.63
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: click chemistry

mp

132-143 °C

storage temp.

−20°C

SMILES string

C(N(Cc1cn(Cc2ccccc2)nn1)Cc3cn(Cc4ccccc4)nn3)c5cn(Cc6ccccc6)nn5

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 key

WKGZJBVXZWCZQC-UHFFFAOYSA-N

Application

A polytriazolylamine ligand which stabilizes Cu(I) towards disproportionation and oxidation thus enhancing its catalytic effect in the azide-acetylene cycloaddition.

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Hazard Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Polytriazolylamines were synthesized by the copper(I)-catalyzed ligation of azides and alkynes. The C3-symmetric derivative, TBTA, was shown to be a powerful stabilizing ligand for copper(I), protecting it from oxidation and disproportionation, while enhancing its catalytic activity.
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The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either

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