![1-[(2-Propynyloxy)methyl]pyrene](/images/structure-default.jpg)
1-[(2-Propynyloxy)methyl]pyrene | CAS 1115084-83-7
| Catalog Number | F08-0016 |
| Category | Pyrene Dyes |
| Molecular Formula | C20H14O |
| Molecular Weight | 270.33 |
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Product Introduction
1-[(2-Propynyloxy)methyl]pyrene is a fluorescent probe that features a pyrene chromophore known for its strong aromatic conjugation and distinctive excimer emission. This compound is equipped with an alkyne group, facilitating its role as a bioorthogonal fluorescent tag through click chemistry reactions, enabling selective labeling of biomolecules in complex environments. In fluorescence imaging workflows, 1-[(2-Propynyloxy)methyl]pyrene is utilized for its ability to participate in energy transfer processes, making it a valuable component in the study of molecular interactions and dynamics.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | 1-(prop-2-ynoxymethyl)pyrene; 1-(Propargyloxymethyl)pyrene; 1-[(Propargyloxy)methyl]pyrene |
| Purity | >98.0%(GC) |
| IUPAC Name | 1-(prop-2-ynoxymethyl)pyrene |
| SMILES | C#CCOCC1=C2C=CC3=CC=CC4=C3C2=C(C=C4)C=C1 |
| InChI | InChI=1S/C20H14O/c1-2-12-21-13-17-9-8-16-7-6-14-4-3-5-15-10-11-18(17)20(16)19(14)15/h1,3-11H,12-13H2 |
| InChIKey | PHLBHJYVJNAPAY-UHFFFAOYSA-N |
| Appearance | Solid |
| Melting Point | 85 °C |
Product Specification
| Signal | Warning |
| GHSHazardStatements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] |
| Precautionary Statement Codes | P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Application
1-[(2-Propynyloxy)methyl]pyrene is a pyrene-based fluorescent labeling building block bearing a propargyl ether (alkyne) handle for post-functionalization workflows. The pyrene chromophore is widely used as a strong fluorescence reporter for tracking hydrophobic environments and for constructing fluorescence tagging reagents, while the terminal alkyne enables chemoselective conjugation strategies commonly used in chemical biology and materials labeling. In practice, this reagent is leveraged to introduce a fluorescent pyrene tag onto biomolecule-derived scaffolds, polymers, and surfaces where click-compatible attachment is required.
1. Biomolecule Fluorescent Tagging
1-[(2-Propynyloxy)methyl]pyrene is used to prepare fluorescent conjugates for labeling proteins, peptides, and other biomolecule-derived materials in research workflows that rely on alkyne-functional handles. Researchers incorporate the pyrene reporter into biomolecule conjugation strategies to enable sensitive visualization and tracing in microscopy-based studies and fluorescence readouts, benefiting from pyrene's strong emission and its utility as an environment-sensitive probe. The propargyl ether functionality supports downstream attachment to azide-bearing partners, making it a practical reagent for building fluorescent bioconjugates used in labeling studies, binding assays, and material-biomolecule interaction experiments.
2. Polymer And Surface Labeling
1-[(2-Propynyloxy)methyl]pyrene is commonly employed to introduce fluorescent pyrene tags into polymers and to functionalize material surfaces for optical tracking and materials characterization. In polymer science and biomaterials research, the reagent is used to generate click-compatible fluorescent materials where the alkyne handle can be incorporated into coatings, hydrogels, or polymer networks and then coupled to azide-functional components. This approach supports studies of material assembly, surface modification verification, and spatial mapping of labeled domains using fluorescence microscopy, where pyrene provides a robust reporter for tracking labeled regions within complex matrices.
3. Fluorescent Probe Construction
1-[(2-Propynyloxy)methyl]pyrene serves as a modular fluorophore component for constructing fluorescence probes and labeling reagents that require a click-reactive attachment point. Chemical biology teams use pyrene-tagged conjugates to build probe formats for monitoring binding events, tracking probe localization, or generating fluorescent standards for assay development, where the alkyne enables controlled incorporation into larger probe architectures. The resulting pyrene-containing constructs are frequently used in fluorescence-based experiments that benefit from a stable, bright reporter and a flexible attachment strategy for assembling multicomponent imaging or sensing reagents.
4. Hydrophobic Environment Tracing
1-[(2-Propynyloxy)methyl]pyrene is applied as a fluorescent reporter to track hydrophobic microenvironments created within micelles, membranes, and other phase-separated systems. Researchers use pyrene fluorescence to monitor changes in local environment around the labeled moiety, supporting studies of partitioning, assembly, and compartmentalization in membrane-mimetic and soft-matter systems. The propargyl ether handle also allows the pyrene reporter to be incorporated into click-attachable constructs, enabling controlled placement of the fluorophore within larger labeled architectures used for fluorescence imaging and comparative fluorescence measurements.
Computed Properties
| XLogP3 | 4.8 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 3 |
| Exact Mass | 270.104465066 g/mol |
| Monoisotopic Mass | 270.104465066 g/mol |
| Topological Polar Surface Area | 9.2Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 419 |
| 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 |
|---|---|---|
| US-10669250-B2 | Hypervalent iodine CF2CF2X reagents and their use | 2014-08-07 |
| US-2019040036-A1 | Hypervalent iodine cf2cf2x reagents and their use | 2014-08-07 |
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