149806-75-7

Usage

Main properties

1. Molecular formula: C9H9N3O2
2. Contains an azido group and an ethoxy group attached to the fourth position
3. Used in organic synthesis
4. Ability to undergo various chemical reactions
5. Starting material for nitrogen-containing organic molecules
6. Potential applications in medicinal chemistry and pharmaceutical research

Chemical structure

Contains a benzaldehyde backbone with an azido group (-N3) and an ethoxy group (-OCH2CH3) attached to the fourth carbon

Reactivity

Can undergo nucleophilic substitution and azide-alkyne Huisgen cycloaddition reactions

Organic synthesis

Used as a building block or intermediate in the synthesis of organic compounds

Medicinal chemistry

Potential applications in the development of new pharmaceuticals or biologically active molecules due to its unique structure and reactivity.

Upstream product

• 52191-15-8 4-(2-bromoethyloxy)benzaldehyde 
• 22042-73-5 4-(2-hydroxy-ethoxy)-benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 75178-70-0 2-azido-O-methanesulphonyl-ethanol 
• 113738-22-0 tosylethylazide 
• 327077-87-2 2-(4-formylphenoxy)ethyl 4-methylbenzenesulfonate 

Downstream Products

• 948017-37-6 [4-(2-azidoethoxy)benzylidene]-malononitrile 
• 1583273-70-4 C₃₂H₃₄N₈O₂ 
• 1613726-71-8 (E)-N'-(4-(2-(4-butyl-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-72-9 (E)-N'-(4-(2-(4-(1-hydroxycyclohexyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-73-0 (E)-N'-(4-(2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-74-1 (E)-(1-(2-(4-((2-isonicotinoylhydrazono)methyl)phenoxy)ethyl)-1H-1,2,3-triazol-4-yl)methylpropionate 
• 1613726-75-2 (E)-N'-(4-(2-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-76-3 (E)-N'-(4-(2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-77-4 (E)-N'-(4-(2-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-78-5 (E)-N'-(4-(2-(4-(p-tolyloxymethyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-79-6 (E)-N'-(4-(2-(4-((4-chlorophenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzylidene)isonicotinohydrazide 
• 1613726-52-5 4-(2-(4-butyl-1H-1,2,3-triazol-1-yl)ethoxy)benzaldehyde 
• 1613726-53-6 4-(2-(4-(1-hydroxycyclohexyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzaldehyde 
• 950768-42-0 4-(2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)ethoxy)benzaldehyde 

Relevant academic research and scientific papers

BODIPY based realtime, reversible and targeted fluorescent probes for biothiol imaging in living cells

Real-time live cell imaging and quantification of biothiol dynamics are important for understanding pathophysiological processes. However, the design and synthesis of rational probes that have reversible and real-time capabilities is still challenging. In

Triazole-appended BODIPY-piperazine conjugates and their efficacy toward mercury sensing

An expeditious synthesis of new click reaction-based BODIPY-piperazine conjugates separated by alkyl spacers (4-7) has been described. The compounds under investigation have been thoroughly characterized by various physicochemical techniques viz., element

Synthesis and evaluation of a [18F]BODIPY-labeled caspase-inhibitor

BODIPYs (boron dipyrromethenes) are fluorescent dyes which show high stability and quantum yields. They feature the possibility of selective 18F-fluorination at the boron-core. Attached to a bioactive molecule and labeled with [18F]fluorine, the resulting compounds are promising tracers for multimodal imaging in vivo and can be used for PET and fluorescence imaging. A BODIPY containing a phenyl and a hydroxy substituent on boron was synthesized and characterized. Fluorinated and hydroxy substituted dyes were coupled to an isatin-based caspase inhibitor via cycloaddition and the resulting compounds were evaluated in vitro in caspase inhibition assays. The metabolic stability and the formed metabolites were investigated by incubation with mouse liver microsomes and LC-MS analysis. Subsequently the fluorophores were labeled with [18F]fluorine and an in vivo biodistribution study using dynamic PET was performed.

Bioorthogonal Turn-On BODIPY-Peptide Photosensitizers for Tailored Photodynamic Therapy

Photodynamic therapy (PDT) leads to cancer remission via the production of cytotoxic species under photosensitizer (PS) irradiation. However, concomitant damage and dark toxicity can both hinder its use. With this in mind, we have implemented a versatile

A novel triphenylamine-BODIPY dendron: Click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

A novel triphenylamine-BODIPY based Schiff base fluorescent probe (TPA-BODIPY-OH) with an emission in the near-infrared (NIR) region was designed and prepared by click reaction. TPA-BODIPY-OH showed three emission bands at 510 nm, 598 nm and 670 nm, and can detect Fe3+ and Hg2+ ions with remarkable fluorescence enhancement in THF/H2O (v/v, 1:1, buffered with 10 mM HEPES pH = 7.4) based on the hydrolysis reaction of the -CN bond, and naked eye detection was realized with an obvious color change. The stoichiometry between the probe and ions was deduced from a Job's plot, which is 1:3 for TPA-BODIPY-OH/Fe3+ and 1:2 for TPA-BODIPY-OH/Hg2+, respectively. The dissociation constant value was found to be 1.35 × 10-16 M for TPA-BODIPY-OH/Fe3+ and 2.06 × 10-11 M for TPA-BODIPY-OH/Hg2+. The low detection limit was calculated from the titration results with the values of 5.15 × 10-7 M for TPA-BODIPY-OH/Fe3+ and 6.81 × 10-7 M for TPA-BODIPY-OH/Hg2+, respectively. In order to investigate the biological applications of TPA-BODIPY-OH, a living cell imaging experiment was carried out. The results demonstrate that TPA-BODIPY-OH can be successfully applied as a bioimaging agent in living cells. In addition, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the TPA-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy. TPA-BODIPY-OH/SiO2 nanoparticles exhibit good dispersibility, and the quantum yield of FNPs at 657 nm was 42.3%.

De Novo Design of Phototheranostic Sensitizers Based on Structure-Inherent Targeting for Enhanced Cancer Ablation

Structure-inherent targeting (SIT) agents are of particular importance for clinical precision medicine; however, there still exists a great lack of SIT phototheranostics for simultaneous cancer diagnosis and targeted photodynamic therapy (PDT). Herein, fo

Bodipy-squaraine triads: Preparation and study of the intramolecular energy transfer, charge separation and intersystem crossing

Two triads (BDP-SQ and Styryl-BDP-SQ) were prepared with Bodipy, styrylBodipy and Squaraine (SQ) units. SQ shows unexpected efficient intersystem crossing (ISC. ΦT = 50%), which is attributed to S1→T1 transition. In the two triads, the F?rster Resonance Energy Transfer (FRET) direction, as well as the spatial localization of the T1 state, was judiciously tuned. The cascade photophysical properties of the triads were studied with steady-state and time-resolved optical spectroscopies, as well as with electrochemical characterization and theoretical computations. We show that triplet state was produced in triad BDP-SQ upon photoexcitation, but in Styryl-BDP-SQ the fast FRET and the charge separation (CS) processes compete with the ISC of the SQ unit, and no triplet state was formed upon photoexcitation. The singlet energy transfer kinetics were found to be 1.6 and 0.6 ps, respectively and are solvent polarity dependent. Charge transfer was confirmed with ultrafast transient absorption spectroscopy.

Photoswitching of the triplet excited state of diiodobodipy-dithienylethene triads and application in photo-controllable triplet-triplet annihilation upconversion

Dithienylethene (DTE)-2,6-diiodoBodipy triads were prepared with the aim to photoswitch the triplet excited state of the 2,6-diiodoBodipy moiety. Bodipy was selected due to its low T1 state energy level to avoid sensitized photocyclization of DTE, which is very often encountered in DTE photoswitches, so that the photochemistry of DTE and the organic chromophore can be addressed independently. This is the first time that DTE was covalently connected with an organic triplet photosensitizer. For the triad with DTE-o structure, selective photoexcitation into the diiodoBodipy part did not initiate photocyclization of DTE-o. Upon photoirradiation at 254 nm, thus the DTE-o → DTE-c transformation, the intersystem crossing (ISC) of 2,6-diiodoBodipy moiety was competed by the photoactivated resonance energy transfer (RET), with Bodipy as the intramolecular energy donor and DTE-c as energy acceptor. The fluorescence of Bodipy was quenched and the triplet state lifetime of Bodipy was reduced from 105.1 to 40.9 μs. The photoreversion is O2-independent, but can be greatly accelerated upon selective photoexcitation into the diiodoBodipy absorption band (at 535 nm). We concluded that ISC is not outcompeted by RET. The photoswitching of the triplet state was transduced to the singlet oxygen photosensitizing, as well as triplet-triplet annihilation upconversion.

Highly efficient energy transfer in the light harvesting system composed of three kinds of boron-dipyrromethene derivatives

A light-harvesting system containing three kinds of BODIPY fluorophores was synthesized. It exhibited very strong absorption in the region from 300 to 700 nm, and the energy transfer within it was highly efficient.

Orienting an Organic Semiconductor into DNA 3D Arrays by Covalent Bonds

A quasi-one-dimensional organic semiconductor, hepta(p-phenylene vinylene) (HPV), was incorporated into a DNA tensegrity triangle motif using a covalent strategy. 3D arrays were self-assembled from an HPV-DNA pseudo-rhombohedron edge by rational design and characterized by X-ray diffraction. Templated by the DNA motif, HPV molecules exist as single-molecule fluorescence emitters at the concentration of 8 mM within the crystal lattice. The anisotropic fluorescence emission from HPV-DNA crystals indicates HPV molecules are well aligned in the macroscopic 3D DNA lattices. Sophisticated nanodevices and functional materials constructed from DNA can be developed from this strategy by addressing functional components with molecular accuracy.