
BDP 581/591 azide | CAS 2183473-20-1
| Catalog Number | F01-0230 |
| Category | BODIPY |
| Molecular Formula | C25H25BF2N6O |
| Molecular Weight | 474.3 |
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Product Introduction
BDP 581/591 alkyne is a linker of BDP which can be used in fluorescence polarization assays. The addition of the azide allows for it to be used in copper-catalyzed Click Chemistry reactions with alkynes, DBCO and BCN.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | N-(3-azidopropyl)-3-(5,5-difluoro-7-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-3-yl)propanamide |
| Purity | 95% |
| IUPAC Name | N-(3-azidopropyl)-3-[2,2-difluoro-12-[(1E,3E)-4-phenylbuta-1,3-dienyl]-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl]propanamide |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)NCCCN=[N+]=[N-])C=C3[N+]1=C(C=C3)C=CC=CC4=CC=CC=C4)(F)F |
| InChI | InChI=1S/C25H25BF2N6O/c27-26(28)33-21(10-5-4-9-20-7-2-1-3-8-20)11-13-23(33)19-24-14-12-22(34(24)26)15-16-25(35)30-17-6-18-31-32-29/h1-5,7-14,19H,6,15-18H2,(H,30,35)/b9-4+,10-5+ |
| InChIKey | OHUOEWAPMDBSIO-LUZURFALSA-N |
| Solubility | DCM, alcohols, DMF, DMSO |
Product Specification
| Excitation | 585 |
| Emission | 594 |
| Storage | -20 °C |
Application
BDP 581/591 azide is an azide-functionalized BODIPY dye designed for copper-free click chemistry labeling workflows where a fluorescent handle is needed for efficient bioconjugation. The BODIPY core provides bright visible fluorescence in the orange-red spectral region, making this reagent useful for constructing fluorescent conjugates, probes, and labeled materials that can be tracked in microscopy and fluorescence-based assays. Its azide group enables attachment to complementary cyclooctyne/DBCO or related strained-alkyne partners under click conditions commonly used in chemical biology.
1. Biomolecule Labeling
BDP 581/591 azide is used by chemical biology and glycobiology labs to install an orange-red BODIPY fluorophore onto proteins, peptides, and other biomolecules via azide-alkyne click conjugation. Researchers typically incorporate the dye into labeling schemes for tracking biomolecule localization, monitoring binding workflows, and generating fluorescent conjugates for downstream imaging or assay readouts. The azide functionality supports modular probe construction, allowing the same fluorophore to be transferred onto different biomolecule scaffolds using standardized click handles.
2. Fluorescent Probe Construction
BDP 581/591 azide is frequently selected for building fluorescence imaging reagents where a robust BODIPY label is required as part of a larger probe architecture. In probe development workflows, the azide group serves as a convenient fluorescent "tag" that can be coupled to targeting motifs, affinity ligands, or scaffold components bearing strained-alkyne groups, enabling researchers to generate modular fluorescent probes for microscopy and fluorescence readouts. This approach is especially useful when probe designers want a consistent fluorophore while varying the recognition or delivery element.
3. Biomaterial Surface Functionalization
BDP 581/591 azide supports fluorescent surface engineering of polymers, hydrogels, and other biomaterial platforms by enabling covalent attachment of the BODIPY label to materials bearing complementary click-reactive groups. Materials scientists and biomaterials groups use the resulting fluorescently labeled surfaces to visualize coating uniformity, track material interactions with cells or biomolecules, and follow adsorption or immobilization processes in fluorescence microscopy. The azide handle enables post-functionalization strategies that integrate the dye into otherwise non-fluorescent material systems without requiring dye incorporation during bulk synthesis.
4. Fluorescence-Based Assay Tracing
BDP 581/591 azide is used as a fluorescent tracer component in fluorescence assay development where an orange-red emitting label is required to follow reagent distribution, binding events, or process kinetics. Assay developers incorporate the dye into conjugates or labeled components through click coupling, then monitor fluorescence in plate readers or imaging systems to generate time-resolved or endpoint measurements. This labeling strategy is commonly applied in research workflows that require stable fluorescent tagging of assay reagents while keeping the conjugation step modular and compatible with multi-component assay designs.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 10 |
| Exact Mass | 474.2150959 g/mol |
| Monoisotopic Mass | 474.2150959 g/mol |
| Topological Polar Surface Area | 51.4Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 992 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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