235095-05-3

Usage

Uses

Used in Chemical Synthesis:
1-Azido-6-bromo-hexane is used as a starting material or intermediate for the synthesis of other complex molecules in the chemical industry. Its unique azido and bromo groups facilitate various chemical reactions, making it a valuable component in the creation of new compounds.
Used in Scientific Research:
1-Azido-6-bromo-hexane is employed as a research tool in the field of organic chemistry. Its reactivity and functional groups allow scientists to explore new reaction pathways and investigate the properties of different chemical structures, contributing to the advancement of chemical knowledge.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-Azido-6-bromo-hexane is used as a building block for the development of new drugs. Its versatility in chemical reactions enables the creation of potential drug candidates with desired properties, such as improved efficacy or reduced side effects.
Used in Material Science:
1-Azido-6-bromo-hexane is utilized in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with enhanced characteristics, such as increased stability or improved performance in specific applications.

Upstream product

• 146292-90-2 6-azidohexan-1-ol 
• 2695-47-8 6-Bromo-1-hexene 
• 4286-55-9 1-bromo-6-hexanol 
• 629-03-8 1 ,6-dibromohexane 

Downstream Products

• 400614-31-5 2,3,6-tri-O-benzyl-α-D-galactopyranosyl-(1->1)-2,3,4-tri-O-benzyl-6-O-(6-azidohexyl)-α-D-glucopyranoside 
• 500567-74-8 5-(6-azido-hexyloxy)-benzene-1,3-dicarbaldehyde 
• 945259-80-3 C₃₆H₇₃N₃O₆ 
• 945259-81-4 C₄₂H₈₄N₆O₆ 
• 1124219-19-7 4-C-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-N-(6-azidohexyl)-4-piperidinol 
• 1144106-76-2 7-(4-(2-(2-azidoethoxy)ethyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1246635-34-6 N-(6-azidohexyl)-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 1338728-76-9 4-(6-azidohexyl)-1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane 
• 1338728-75-8 4-(6-azidohexyl)-1,3-diisopropylimidazol-2-ylidene borane 
• 1338728-96-3 4-(6-azidohexyl)-1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene iodoborane 
• 1338728-98-5 4-(6-aminohexyl)-1,3-bis(2,6-diisopropylphenyl)imidazolium iodide 
• 1338729-00-2 4-(6-(4-(4-bromophenyl)-1,2,3-triazol-1-yl)hexyl)-1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane 
• 1338729-03-5 4-(6-(4-(4-bromophenyl)-1,2,3-triazol-1-yl)hexyl)-1,3-bis(2,6-diisopropylphenyl)imidazolium triflate 
• 1378896-43-5 2-(2-hexyldecyl)-5-(6-azidohexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 

Relevant academic research and scientific papers

Epoxides related to dioncoquinone B: Synthesis, activity against multiple myeloma cells, and search for the target protein

Epoxide 2b is an analog of the synthetic intermediate 2a en route to the polyketide-derived antitumoral naphthoquinone dioncoquinone B (1), isolated from cell cultures of the tropical liana Triphyophyllum peltatum (Dioncophyllaceae). Compound 2b was found to induce strong apoptosis in multiple myeloma cells at a concentration (EC50 = 3.5 μM), distinctly lower than that of 1 and any related analog, without exerting significant toxicity against normal blood cells. Preliminary studies showed that 2b follows different SAR rules as compared to the naphthoquinones. Among the series of synthesized epoxides, 2b was the most active one and was thus, after biotinylation, subjected to mass spectrometry-based affinity capture experiments aiming at the identification of target proteins. The MS data revealed 2b to address proteins that are associated with stress regulation processes which are critical for multiple myeloma cell survival.

Synthesis and photophysical studies on triazole bridged dendrimers with phenothiazine as surface unit

Synthesis and photophysical properties of some novel 1, 2, 3-triazole bridged phenothiazine dendrimers with enone and S-(-)-BINOL core is described. ARKAT-USA, Inc.

Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).

Targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system

The invention relates to a targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system. Sugar functionalized column [5] arene with targeted selectivity isused as a host molecule, a trimethylamine derivative of disulfide bond bridged dicyanomethylene 4H pyran with GSH response fluorescence tracing is used as a guest molecule, a GSH responsive column [5] arene amphiphilic molecule with targeted and fluorescence tracing is prepared through host-guest interaction, nano-vesicles are formed in a solution through hydrophilic-hydrophobic interaction, andan anticancer drug is encapsulated in a vesicle cavity. Mannose is specifically bound with a mannose receptor overexpressed on the surface of a breast cancer cell, so that targeted selective entry into the cancer cell is realized; meanwhile, a disulfide bond is quickly broken under the action of GSH with relatively high concentration in the cancer cell, so that the vesicles are promoted to break to quickly release the anticancer drug; and in addition, the dicyanomethylene 4H pyran is used as a fluorescent chromogenic group to realize fluorescence tracing. The system can be applied to transportation and tracing of the anticancer drug.

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

A Renal-Clearable Duplex Optical Reporter for Real-Time Imaging of Contrast-Induced Acute Kidney Injury

Despite its high morbidity and mortality, contrast-induced acute kidney injury (CIAKI) remains a diagnostic dilemma because it relies on in vitro detection of insensitive late-stage blood and urinary biomarkers. We report the synthesis of an activatable duplex reporter (ADR) for real-time in vivo imaging of CIAKI. ADR is equipped with chemiluminescence and near-infrared fluorescence (NIRF) signaling channels that can be activated by oxidative stress (superoxide anion, O2.?) and lysosomal damage (N-acetyl-β-d-glucosaminidase, NAG), respectively. By virtue of its high renal clearance efficiency (80 % injected doses after 24 h injection), ADR detects sequential upregulation of O2.? and NAG in the kidneys of living mice prior to a significant decrease in glomerular filtration rate (GFR) and tissue damage in the course of CIAKI. ADR outperforms the typical clinical assays and detects CIAKI at least 8 h (NIRF) and up to 16 h (chemiluminescence) earlier.

Monoamine oxidase-A targeting probe for prostate cancer imaging and inhibition of metastasis

Mitochondrial enzyme monoamine oxidase (MAO-A) is known to be overexpressed in prostate cancer (PCa) cells. Herein, we have developed a two-photon probe (PCP-1) for selectively targeting and imaging the MAO-A in PCa. Supported by enzymatic docking and in vitro experiments, PCP-1 showed efficiency to visualize MAO-A overexpressing cells and inhibit their growth and metastasis potential.

Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

Facile Synthesis of Sequence-Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions

The orthogonal sulfur–fluoride exchange reaction (SuFEx) and copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) are employed to synthesize sequence-regulated synthetic polymers. The high efficiency and broad tolerance of SuFEx and CuAAC to diverse chemical functionalities enable the one-pot synthesis of polydispersed sequence-controlled polymers by step-growth copolymerization in high yield and sequence complexity. Furthermore, iterative SuFEx and CuAAC coupling reactions on a solid support, without the need of protecting groups, afford monodispersed sequence-defined oligomers. The use of this orthogonal pair of click reactions provides new opportunities to facilely access sequence-regulated synthetic polymers with a high degree of structural diversity.

GSH-Responsive supramolecular nanoparticles constructed by β-d-galactose-modified pillar[5]arene and camptothecin prodrug for targeted anticancer drug delivery

Supramolecular construction of a targeted and stimuli-responsive drug delivery system is still a challenging task. Herein, GSH-responsive supramolecular prodrug nanoparticles were constructed by the host-guest complexation between a β-d-galactose-functionalized water-soluble pillar[5]arene (GalP5) and a disulfide bond containing camptothecin prodrug (G). The obtained prodrug nanoparticles were stable under physiological conditions, whereas efficient drug release was triggered in a simulated tumor environment with high GSH concentration. In vitro studies revealed that these prodrug nanoparticles preferentially entered asialoglycoprotein receptor-overexpressing HepG2 cells due to the active targeting effect of galactose units. This active targeting effect resulted in the maximization of anticancer efficacy and reduction of the undesirable side effects to normal cells.