166388-57-4

Basic information

• Product Name: 2-[2-(2-Azidoethoxy)ethoxy]ethanamine
• Synonyms: N3-PEG2-CH2CH2NH2;Azido-PEG2-Amine;2-[2-(2-Azidoethoxy)ethoxy]ethanamine;N3-PEG2-NH2
• CAS NO: 166388-57-4
• Molecular Formula: C₆H₁₄N₄O₂
• Molecular Weight: 174.2
• Mol File: 166388-57-4.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Solubility: Soluble in Water, DMSO, DMF, DCM
• CAS DataBase Reference: 2-[2-(2-Azidoethoxy)ethoxy]ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(2-Azidoethoxy)ethoxy]ethanamine(166388-57-4)
• EPA Substance Registry System: 2-[2-(2-Azidoethoxy)ethoxy]ethanamine(166388-57-4)

Safety Data

• Hazardous Substances Data: 166388-57-4(Hazardous Substances Data)

Usage

Description

Azido-PEG2-amine is a bifunctional crosslinker containing an amino and an azide group. The amino group is reactive with carboxylic acids, activated NHS esters,. The azide(N3) group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage.

Synthesis

2-[2-(2-Hydroxyethoxy)ethoxy]ethyl chloride (15 g, 88.9 mmol), NaI(4.06 g, 27.1 mmol), and NaN3 (45.3 mg, 697 mmol) were dissolved in distilled water (90 mL), and the solution was stirred for 48 h at 50 °C. The reaction mixture extracted with ethyl acetate for three times. The organic layer was dried over Na2SO4 , and evaporated to collect 2-[2-(2-azidoethoxy)ethoxy]ethanol (14.0 g, 90.1%) as a yellow oil.To the solution 2-[2-(2-azidoethoxy)ethoxy]ethanol (8 g, 45.7 mmol) in THF (22.4 mL), 6 M NaOH(20.8 mL) and TsCl (13.1 g, 68.6 mmol) were added at 0 °C. The reaction mixture was stirred for 1 h at room temperature under nitrogen atmosphere. The solution was then extracted with diethyl ether four times, and the organic layer was washed with 1 M NaOH. After evaporation of the organic layer,2-[2-(2-azidoethoxy)ethoxy]ethyl tosylate (16.8 g, 98.6%) was obtained as a yellow oil.Finally, ammonia solution (28%, 14.8 mL, 365 mol) was added to the 2-[2-(2-azidoethoxy)ethoxy]-ethyl tosylate (8 g, 24.3 mmol) dissolved in THF (95.9 mL), and reaction mixture was stirred for 96 h at 40 °C. After the reaction, distilled water (50 mL) was added to the solution. The mixture was washed with diethyl ether and then extracted with dichloromethane. The organic layer was dried over NaSO4 and evaporated to obtain 2-[2-(2-azidoethoxy)ethoxy]ethanamine (2.49 g, 58.8%) as a yellow oil.

Upstream product

• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 

Downstream Products

• 1233927-49-5 C₂₆H₃₈F₃N₇O₈ 
• 1417539-34-4 tris{4-(4-{2-[2-(2-azidoethoxy)ethoxy]ethylaminocarbonyloxy}butyn-1-yl)phenyl}methane 
• 945633-30-7 N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide 
• 1412905-19-1 4-((N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)acetamido)methyl)-2,6-diisopropylphenyl 4-oxo-5-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanamido)pentanoate 
• 1412905-22-6 N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-N-(4-hydroxy-3,5-diisopropylbenzyl)acetamide 

Relevant articles and documents

Adaptive amphiphilic dendrimer-based nanoassemblies as robust and versatile siRNA delivery systems

siRNA delivery remains a major challenge in RNAi-based therapy. Here, we report for the first time that an amphiphilic dendrimer is able to self-assemble into adaptive supramolecular assemblies upon interaction with siRNA, and effectively delivers siRNAs to various cell lines, including human primary and stem cells, thereby outperforming the currently available nonviral vectors. In addition, this amphi-philic dendrimer is able to harness the advantageous features of both polymer and lipid vectors and hence promotes effective siRNA delivery. Our study demonstrates for the first time that dendrimer-based adaptive supramolecular assemblies represent novel and versatile means for functional siRNA delivery, heralding a new age of dendrimer-based self-assembled drug delivery in biomedical applications.

DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX

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Catalytic Synthesis of PEGylated EGCG Conjugates that Disaggregate Alzheimer's Tau

The naturally occurring flavonoid ( )-epigallocatechin gallate (EGCG) is a potent disaggregant of tau fibrils. Guided by the recent cryo-electron microscopy (cryoEM) structure of EGCG bound to fibrils of tau derived from an Alzheimer s brain donor, methods to site-specifically modify the EGCG D-ring with aminoPEGylated linkers are reported. The resultant molecules inhibit tau fibril seeding by Alzheimer s brain extracts. Formulations of aminoPEGylated EGCG conjugated to the (quasi)-brain-penetrant nanoparticle Ferumoxytol inhibit seeding by AD-tau with linker length affecting activity. The protecting groupfree catalytic cycloaddition of amino azides to mono-propargylated EGCG described here provides a blueprint for access to stable nanoparticulate forms of EGCG potentially useful as therapeutics to eliminate Alzheimer s-related tau tangles.