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Tri(propargyl-NHCO-ethyloxyethyl)amine
| Catalog Number | R01-0081 |
| Category | Alkynes |
| Molecular Formula | C24H36N4O6 |
| Molecular Weight | 476.6 |
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Product Introduction
Tri(propargyl-NHCO-ethyloxyethyl)amine is a trivalent compound featuring three propargyl groups, which are alkyne functionalities known for their participation in copper-catalyzed azide–alkyne cycloaddition reactions. This molecular architecture makes it suitable for applications in click chemistry, particularly in the design of multifunctional linkers and surface modification strategies. The compound's structural configuration facilitates its incorporation into complex macromolecular assemblies, enabling efficient bioconjugation and polymer functionalization processes.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Purity | 98% |
| IUPAC Name | 3-[2-[bis[2-[3-oxo-3-(prop-2-ynylamino)propoxy]ethyl]amino]ethoxy]-N-prop-2-ynylpropanamide |
| SMILES | C#CCNC(=O)CCOCCN(CCOCCC(=O)NCC#C)CCOCCC(=O)NCC#C |
| InChI | InChI=1S/C24H36N4O6/c1-4-10-25-22(29)7-16-32-19-13-28(14-20-33-17-8-23(30)26-11-5-2)15-21-34-18-9-24(31)27-12-6-3/h1-3H,7-21H2,(H,25,29)(H,26,30)(H,27,31) |
| InChIKey | IREDTJVEYMNUME-UHFFFAOYSA-N |
| Solubility | Water, DMSO, DCM, DMF |
Product Specification
| Storage | -20 °C |
Application
Tri(propargyl-NHCO-ethyloxyethyl)amine is a multi-functional propargylated amine designed for copper-free and/or copper-mediated click chemistry workflows, enabling efficient installation of multiple alkyne handles on biomolecules, polymers, and surfaces. As a tri-propargyl scaffold, it provides three reactive termini that are well-suited to building multivalent conjugates, crosslinked networks, and imaging or detection platforms that rely on orthogonal reactivity. Its ethyloxyethyl carbamate motif supports solubility and stable handle presentation, making it a practical reagent for downstream bioconjugation and materials labeling where high local density of clickable groups improves labeling efficiency and construct uniformity.
1. Multivalent Biomolecule Labeling
Tri(propargyl-NHCO-ethyloxyethyl)amine is commonly used to introduce multiple alkyne functionalities onto proteins, peptides, and nucleic-acid-associated carriers for subsequent click-based conjugation. Researchers value the tri-valent architecture when they need denser labeling for affinity reagents, multivalent binding constructs, or standardized probe libraries where the number of attachment points influences signal intensity and conjugate stability. The reagent’s carbamate-protected propargyl groups help maintain reactive handle availability during typical bioconjugation workflows, supporting reproducible downstream coupling to azide-bearing partners used in chemical biology and assay development.
2. Surface Functionalization And Coatings
Tri(propargyl-NHCO-ethyloxyethyl)amine is applied in materials science settings to create alkyne-rich surfaces that can be patterned or uniformly functionalized for later click attachment of polymers, biomolecules, and affinity ligands. This use case is prevalent in the fabrication of clickable coatings, microarray surfaces, and sensor interfaces where controlled presentation of reactive groups enables modular assembly of functional layers. By leveraging the tri-propargyl scaffold, teams can improve the probability of productive surface-to-surface or surface-to-probe coupling, which is particularly useful when immobilizing bulky azide-containing reagents or building multilayer constructs for imaging and diagnostics reagent platforms.
3. Hydrogel And Polymer Crosslinking
Tri(propargyl-NHCO-ethyloxyethyl)amine supports the preparation of clickable polymer networks and hydrogels that can be assembled or remodeled through azide-alkyne cycloaddition strategies. In biomaterials workflows, the tri-alkyne functionality helps translate bulk polymer properties into tunable crosslink density, enabling materials engineers to design scaffolds and encapsulation matrices with defined attachment points for later incorporation of bioactive motifs or reporter components. The reagent is also used to generate alkyne-bearing polymer intermediates that can be stored as functional building blocks and then coupled to azide-modified counterparts during construct assembly.
4. Molecular Imaging And Probe Building
Tri(propargyl-NHCO-ethyloxyethyl)amine is frequently incorporated into probe design pipelines where alkyne handles are required for modular attachment of fluorophores, affinity tags, or imaging moieties that are delivered as azide-functionalized components. Chemical biology groups use tri-propargyl reagents to build multivalent imaging probes that can be assembled from standardized azide-labeled reporters, improving flexibility in probe generation and facilitating rapid iteration across labeling schemes. The multi-handle format also supports higher local loading of imaging reporters on carrier scaffolds, which is advantageous for developing robust research-grade detection reagents and mechanistic study tools.
Computed Properties
| XLogP3 | -2.1 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 21 |
| Exact Mass | 476.26348488 g/mol |
| Monoisotopic Mass | 476.26348488 g/mol |
| Topological Polar Surface Area | 118Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 642 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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