86770-70-9

Usage

Uses

Used in Organic Synthesis:
((2-(2-(2-azidoethoxy)ethoxy)ethoxy)methyl)benzene is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of a wide range of complex organic molecules.
Used in Click Chemistry:
In the field of click chemistry, ((2-(2-(2-azidoethoxy)ethoxy)ethoxy)methyl)benzene is used as a reactant for its azide group, which allows for efficient and selective reactions, particularly the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. This reaction is highly useful for the rapid and modular assembly of complex molecules and macromolecules.
Used in the Production of Nitrogen-Containing Compounds:
The presence of the azide group in ((2-(2-(2-azidoethoxy)ethoxy)ethoxy)methyl)benzene makes it a valuable precursor in the synthesis of nitrogen-containing compounds, which are important in various chemical and pharmaceutical applications.
Used in Research and Development:
((2-(2-(2-azidoethoxy)ethoxy)ethoxy)methyl)benzene is also utilized in research and development settings to explore new reaction pathways, develop novel synthetic methods, and investigate the properties of complex organic molecules, including their potential applications in material science, pharmaceuticals, and other industries.

Upstream product

• 55489-58-2 triethylene glycol monobenzyl ether 
• 702701-70-0 methanesulfonic acid 2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethyl ester 
• 100-39-0 benzyl bromide 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 100-44-7 benzyl chloride 
• 105891-50-7 1-chloro-10-phenyl-3,6,9-trioxadecane 
• 84131-04-4 triethylene glycol monobenzyl tosyl ether 

Downstream Products

• 139115-92-7 tert-butyl 2-(2-(2-hydroxyethoxy)ethoxy)ethylcarbamate 
• 6338-55-2 2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol 
• 86770-75-4 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethan-1-amine 

Relevant academic research and scientific papers

A MedChem toolbox for cereblon-directed PROTACs

A modular chemistry toolbox was developed for cereblon-directed PROTACs. A variety of linkers was attached to a CRBN ligand via the 4-amino position of pomalidomide. We used linkers of different constitution to modulate physicochemical properties. We equipped one terminus of the linker with a set of functional groups, e.g. protected amines, protected carboxylic acids, alkynes, chloroalkanes, and protected alcohols, all of which are considered to be attractive for PROTAC design. We also highlight different opportunities for the expansion of the medicinal chemists' PROTAC toolbox towards heterobifunctional molecules, e.g. with biotin, fluorescent, hydrophobic and peptide tags.

A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin

Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.

Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues

Engagement of toll-like receptors serve to link innate immune responses with adaptive immunity and can be exploited as powerful vaccine adjuvants for eliciting both primary and anamnestic immune responses. TLR7 agonists are highly immunostimulatory without inducing dominant proinflammatory cytokine responses. A structure-activity study was conducted on the TLR7-agonistic imidazoquinolines, starting with 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4, 5-c]quinolin-1-yl)-2-methylpropan-2-ol as a lead. Modifications of the secondary amine of the C2 ethylaminomethylene side chain are poorly tolerated. The 4-amino group must be retained for activity. Replacement of the imidazole ring of the scaffold with triazole or cyclic urea led to complete loss of activity. A systematic exploration of N1-benzyl-C2-alkyl substituents showed a very distinct relationship between alkyl length and TLR7-agonistic potency with the optimal compound bearing a C2-n-butyl group. Transposition of the N 1 and C2 substituents led to the identification of an extremely active TLR7-agonistic compound with an EC50 value of 8.6 nM. The relative potencies in human TLR7-based primary reporter gene assays were paralleled by interferon-α induction activities in whole human blood models.

Lack of effect of the length of oligoglycine- and oligo(ethylene glycol)-derived para-substituents on the affinity of benzenesulfonamides for carbonic anhydrase II in solution

Using 1H NMR spectroscopy, values of T2 have been determined for the methylene protons of the oligoglycine moieties of para-substituted benzenesulfonamides having structures H2NO2SC6H4CO(Gly)(n)OH (n = 1-6) bound at the active site of bovine carbonic anhydrase II (CA, EC 4.2.1.1). These values have been correlated with measurements of dissociation constants of these complexes, in order to infer motion of these ligands when bound to the enzyme. Motion of glycines 1-3 (those closest to the aryl ring) is hindered by their proximity to the protein; motion of glycines 4-6 is relatively unhindered. Despite the restriction to motion inferred for glycines 1-3, the values of K(d) for the six compounds (n = 1-6, 1-6) are indistinguishable within experimental uncertainty (± 20%): K(d) in μM (n) 0.30 (1); 0.26 (2); 0.33 (3); 0.37 (4); 0.37 (5); 0.34 (6). There is, therefore, an unexpected compensation of the loss in conformational entropy on binding by another contributor to the free energy.