
Pyrene azide 2 | CAS 1807512-45-3
| Catalog Number | F08-0008 |
| Category | Pyrene Dyes |
| Molecular Formula | C24H24N4O3 |
| Molecular Weight | 416.47 |
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Product Introduction
Pyrene azide 2 is a fluorescent probe featuring a polycyclic aromatic hydrocarbon structure known for its strong blue fluorescence. It contains an azide functional group that enables bioorthogonal conjugation with alkyne-modified biomolecules through a copper-catalyzed azide-alkyne cycloaddition reaction, facilitating its use in labeling applications. Pyrene azide 2 is often incorporated into fluorescence imaging workflows and biosensing assays, where it participates in energy transfer processes due to its ability to act as a donor in Förster resonance energy transfer (FRET) experiments.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Purity | NMR 1H (95%) |
| IUPAC Name | N-[2-[2-(2-azidoethoxy)ethoxy]ethyl]-2-pyren-1-ylacetamide |
| SMILES | C1=CC2=C3C(=C1)C=CC4=C(C=CC(=C43)C=C2)CC(=O)NCCOCCOCCN=[N+]=[N-] |
| InChI | InChI=1S/C24H24N4O3/c25-28-27-11-13-31-15-14-30-12-10-26-22(29)16-20-7-6-19-5-4-17-2-1-3-18-8-9-21(20)24(19)23(17)18/h1-9H,10-16H2,(H,26,29) |
| InChIKey | UVMVZDBLWRBVGT-UHFFFAOYSA-N |
| Solubility | Good solubility in chloroform, dichloromethane, moderate solubility in DMSO, DMF, acetonitrile |
| Appearance | Yellowish solid |
Product Specification
| Excitation | 343; 326; 313; 276; 265; 242; 234 |
| Emission | 377; 397 |
| Storage | Storage: 24 months after receival at -20 °C in the Dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. |
Application
Pyrene azide 2 is an azide-functionalized pyrene fluorophore designed for click chemistry labeling workflows. Its polycyclic aromatic pyrene core provides strong fluorescence for visualization and tracking, while the azide handle enables efficient conjugation to complementary alkynes in bioconjugation and materials functionalization. This combination makes Pyrene azide 2 useful as a fluorescent tag for constructing labeled biomolecules, probes, and engineered surfaces where robust aromatic fluorescence is desired.
1. Fluorescent Bioconjugation Labeling
Pyrene azide 2 is commonly used as a fluorescent labeling reagent in click chemistry bioconjugation workflows where an azide-bearing fluorophore is required. Researchers incorporate it into peptides, proteins, or other biomolecule constructs by first installing the azide functionality on the target (or using an azide-bearing labeling strategy) and then performing copper-free or copper-catalyzed azide-alkyne cycloaddition with an alkyne-bearing partner. The resulting pyrene-labeled conjugates are used for fluorescence microscopy, fluorescence tracking of conjugate formation, and qualitative localization studies in chemical biology and biomaterials research.
2. Fluorescent Probe Construction
Pyrene azide 2 supports fluorescent probe development where a bright, aromatic fluorophore is needed as a reporter unit. In probe assembly, the azide group serves as a modular handle to attach the pyrene fluorophore to recognition elements, linkers, or scaffolds through click-compatible coupling partners. Typical use cases include building fluorescent labeling reagents for assay development, generating imaging probes for material-associated targets, and creating reference standards for fluorescence-based readouts in screening workflows that rely on pyrene emission.
3. Biomaterial And Surface Functionalization
Pyrene azide 2 is frequently applied in biomaterials science to introduce a fluorescent tag onto engineered polymers, hydrogels, and functional surfaces using click chemistry. By coupling the azide fluorophore to alkyne-functionalized materials, labs can create fluorescently traceable coatings, scaffolds, or surface layers for studying adsorption, immobilization, and material-biomolecule interactions. This approach is especially useful when the fluorescent label needs to remain covalently associated with the material to enable wash-resistant imaging during microscopy or fluorescence-based characterization.
4. Hydrophobic Labeling And Tracing Studies
Pyrene azide 2 is leveraged for fluorescence tracing in systems where hydrophobic/aromatic fluorophore reporters provide strong signal for monitoring distribution and incorporation. Researchers use pyrene-labeled conjugates to follow uptake or association with polymer domains, lipid-like environments, or hydrophobic regions in composite materials. The azide functionality enables modular attachment to the desired carrier or scaffold, allowing the fluorescent reporter to be introduced at defined stages of materials preparation and then visualized by standard fluorescence imaging workflows.
Computed Properties
| XLogP3 | 4.9 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 11 |
| Exact Mass | 416.18484064 g/mol |
| Monoisotopic Mass | 416.18484064 g/mol |
| Topological Polar Surface Area | 61.9Ų |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 638 |
| 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 |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| EP-3399967-A2 | Selective killing of tumors of the hematopoietic and lymphoid tissues | 2016-01-05 |
| US-2019022032-A1 | Selective killing of tumors of the hematopoietic and lymphoid tissues | 2016-01-05 |
| WO-2017120296-A2 | Selective killing of tumors of the hematopoietic and lymphoid tissues | 2016-01-05 |
| US-10905658-B2 | Methods and compositions for detecting hematopoietic and lymphoid tissue cancer cells | 2016-01-05 |
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