This compound belongs to the class of organic compounds known as azo imides. These are n-Imides of azo compounds, analogous to azoxy compounds, having a delocalized structure.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
No vendor-validated analytical or bioassay protocols are provided for this item. Typical uses follow standard literature procedures:
CuAAC/SPAAC ligations for installing triazole-linked tags or conjugates on alkynyl partners (see Reaction Conditions tab for starting parameters).
Alcohol activation (tosylation/mesylation) followed by substitution or coupling to surfaces/polymers.
For step-by-step instructions tailored to your system (substrate loadings, solvent system compatibility with the supplied solution, and purification), consult peer-reviewed protocols and adjust based on the CoA-disclosed concentration and solvent.
Biological Roles
Item-specific: This product is supplied for research use only. No biological role is claimed for the material itself.
Literature context (not product claims)
The compound functions as a chemical handle rather than a metabolite. The terminal azide is bioorthogonal—generally absent from native biochemistry—making it valuable for labeling and conjugation strategies in chemical biology.
The primary alcohol and PEG-like spacer contribute to water compatibility and can reduce nonspecific binding when incorporated into probes or surfaces.
In bioconjugation workflows, azides are introduced into biomolecules (or materials) followed by click to alkynes, enabling installation of fluorophores, affinity tags, or other functional units. The alcohol can be used for upstream attachment (e.g., carbonate linkage) to carriers or scaffolds.
Safety note in bio-context
Although frequently used in bioorthogonal chemistry, this reagent is not intended for in vivo use or therapeutic applications. Handle per SDS and institutional safety practices.
Buffer Applications
This compound is not a buffering agent and is not used to establish or maintain pH. However, its azide functionality supports bioorthogonal ligations that can be carried out in common buffers.
Literature guidance
SPAAC reactions proceed efficiently in neutral aqueous buffers (e.g., PBS, HEPES, pH ~7.2–7.5), often with 0–20% DMSO for solubilization when needed.
CuAAC can be executed in buffered aqueous/organic mixtures (e.g., phosphate buffer with t-BuOH or EtOH) using CuSO4/sodium ascorbate; maintain pH near neutral to protect sensitive partners.
For buffer recipes, ionic strength, and compatibility with specific biomolecules, optimize empirically; confirm the supplied solution solvent to ensure miscibility with the chosen buffer.
Green Alternatives
Because 2-[2-(2-azidoethoxy)ethoxy]ethanol is a specialized reagent rather than a process solvent, greener practice focuses on media and catalysts for its key transformations.
Greener media choices (literature)
Favor water or water/alcohol mixtures for CuAAC and SPAAC where solubility permits. Ethanol/water often provides an effective, low-toxicity alternative to DMF or DMSO.
Use bio-derived solvents (2-MeTHF, Cyrene) for alcohol derivatizations when compatible with reagents; however, ensure azide stability and reagent solubility.
Catalyst considerations (literature)
CuAAC: employ catalytic copper with ligand accelerators (e.g., THPTA) to minimize copper loading; recover copper by chelation/scavenging.
SPAAC eliminates copper altogether but uses strained alkynes; balance reduced metal use against the footprint of strained-alkyne synthesis.
Trade-offs: sometimes slower kinetics; may require ligand optimization
SPAAC vs CuAAC
Pros: metal-free, biocompatible
Trade-offs: cost/availability of strained alkynes; occasionally slower or less selective without guidance from copper ligation chemistry
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is supplied for research use only.
Literature context (non-clinical)
PEG-like azido alcohols are commonly used as linkers or spacers in the synthesis of research-grade conjugates (e.g., small-molecule probes, affinity tags) by click chemistry.
The hydrophilic spacer can improve aqueous handling and reduce aggregation in formulation development studies at the research scale.
Practical notes
If considering pre-formulation or device-coating studies, verify residual metals and solvent composition on the CoA/Spec Sheet.
Avoid making any inference of safety/efficacy; this product is not intended for human or veterinary use.
Physical Properties
Item-specific specifications (this product):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Concentration of solution: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed general properties for the neat compound (for reference; not product specifications):
Molecular formula: C6H13N3O3 (computed from structure)
Molecular weight: ~175.19 g/mol (computed)
Physical state: typically a low-volatility liquid given the triethylene glycol backbone and hydrogen bonding (literature expectation)
Polarity: hydrophilic; contains one hydroxyl and two ether oxygens (literature)
Solubility: expected to be miscible with polar organic solvents (MeOH, EtOH, acetone, acetonitrile, DMF, DMSO) and highly soluble in water due to PEG-like segment (literature)
LogP: anticipated low (hydrophilic) owing to multiple heteroatoms (literature trend)
Boiling point, melting point, density, refractive index, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. For design purposes, treat as a high-boiling, water-miscible organic liquid.
Notes:
Because this is supplied as a solution of unspecified concentration, bulk properties of the neat material may not reflect the behavior of the catalog item. Verify solution solvent and concentration on the CoA before relying on numerical values for method development.
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Solution solvent and concentration: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research-grade reagents are suitable for most synthetic and analytical workflows. Where chromatographic or bioorthogonal applications impose stricter limits (e.g., low-metal, low-peroxide, or low-UV background), HPLC or “bioorthogonal” grades may be preferred.
For click chemistry (CuAAC/SPAAC), trace metal content can influence background or side reactions. If metal-sensitive applications are intended, verify metal specifications on the CoA.
For photochemical work, low-UV-absorbance solvent and minimal chromophoric impurities are beneficial; verify UV cutoff or absorbance specs if critical.
Practical tips
Request and retain the lot-specific CoA for exact solution concentration, solvent system, water content, residual metals, and any stabilizers.
If the solution is intended for bioconjugation, consider a brief polish (e.g., filtration through neutral alumina to remove adventitious copper after CuAAC) only if compatible with the solvent system; avoid drying to neat to minimize azide handling risk.
Perform a small-scale pilot reaction to confirm performance before committing valuable substrates.
Reaction and Applications
Key utility arises from the orthogonal pairing of a terminal azide and a primary alcohol connected by a short PEG spacer.
Click chemistry handles (literature)
CuAAC with terminal alkynes to form 1,4-disubstituted 1,2,3-triazoles; the PEG-like segment imparts hydrophilicity and spacing between conjugation partners (useful in materials and bioconjugation).
SPAAC with strained alkynes (DBCO, BCN) for copper-free ligations in aqueous systems.
Strain-promoted azide–alkyne cycloaddition tolerates buffers and biomolecule contexts; the alcohol can be used to tether to surfaces or further derivatize.
Alcohol derivatization (literature)
Mesylation/tosylation of the primary alcohol to form a leaving group, enabling nucleophilic substitution or further chain extension while retaining the azide.
Carbonate or carbamate formation for protective group strategies or attachment to solid supports.
Oxidation of the alcohol to an aldehyde (e.g., TEMPO/BAIB) or acid (e.g., TEMPO/NaOCl–NaClO2) to diversify functionality prior to click.
Polymer and surface modification (literature)
Grafting to/from reactions on oxides or polymer backbones after converting OH to silanes, phosphates, or acrylates; subsequent azide click introduces triazole-linked motifs.
Practical tips
Keep copper levels controlled in CuAAC to minimize side reactions; use CuSO4/ascorbate with TBTA or THPTA ligands for sensitive substrates.
Avoid strong acids or high heat that could induce azide decomposition; conduct scale-ups with calorimetric awareness and do not distill to dryness.
Reaction Conditions
General, literature-based conditions for common transformations of 2-[2-(2-azidoethoxy)ethoxy]ethanol (guidance only; optimize per substrate):
CuAAC (azide + terminal alkyne → 1,2,3-triazole)
Solvent: t-BuOH/H2O (1:1) or EtOH/H2O; alternatives MeCN/H2O, DMSO/H2O
Temp/Time: RT, 0.5–24 h depending on partners and concentration
Staudinger reduction (to primary amine)
Reagents: PPh3 (1.1–1.5 equiv), H2O
Solvent: THF/H2O or dioxane/H2O
Temp/Time: RT to 50 °C, 2–12 h; follow by hydrolysis of iminophosphorane
Alcohol activation (tosylation/mesylation)
Reagents: TsCl or MsCl (1.1–1.5 equiv), Et3N or pyridine (2–3 equiv)
Solvent: dry DCM, THF, or MeCN
Temp/Time: 0 °C to RT, 1–4 h
Oxidation to aldehyde (TEMPO)
Reagents: TEMPO (2–5 mol%), NaOCl or BAIB as oxidant; NaHCO3 buffer
Solvent: EtOAc/H2O or MeCN/H2O
Temp/Time: 0–5 °C to RT, 0.5–2 h
Notes: Monitor by LC/MS or 1H NMR. Maintain moderate concentrations (≤0.2 M in azide) and avoid concentrating to dryness. For aqueous work, verify the supplied solution solvent to ensure miscibility.
Safety and Handling
Item-specific hazard statements:
Signal word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety considerations for organic azides and azido alcohols (literature guidance; defer to SDS for authoritative data):
Organic azides can be energetic and may decompose exothermically at elevated temperatures or upon strong shock/friction. This azide is embedded in a short PEG-like backbone, which typically lowers volatility and handling risk, but standard azide precautions remain prudent.
Avoid heating to dryness; keep away from strong oxidizers, reducing agents capable of nitrene formation, and strong acids that can accelerate azide decomposition.
Prevent contact with transition metals and their salts during storage to avoid catalytic decomposition. Use plastic or passivated stainless tools; avoid copper surfaces unless in a controlled reaction setup.
PPE and hygiene
Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of vapors/aerosols.
Wash thoroughly after handling; avoid skin and eye contact.
First aid (overview; consult SDS)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Storage and stability
Store at 2–8 °C as specified; keep container tightly closed, protected from light, heat, and ignition sources.
Do not freeze unless the CoA indicates compatibility of the solution matrix with freezing.
Always consult the product-specific SDS for definitive hazard, exposure limits, and spill/cleanup procedures.
Solvent Selection
This product is a reagent supplied as a solution and is not typically used as a bulk solvent. Selection considerations therefore focus on solvents for reactions employing this azido alcohol.
General miscibility and polarity (literature)
Highly polar and hydrophilic; expected to be miscible with water and polar organics (MeOH, EtOH, iPrOH, acetone, MeCN, DMF, DMSO) due to the PEG-like backbone.
Low volatility; compatible with higher-boiling polar aprotics for coupling steps and with water/alcohol mixtures for click chemistry.
Choosing media by application (literature guidance)
CuAAC (click to terminal alkynes): t-BuOH/H2O, EtOH/H2O, or MeCN/H2O with CuSO4/sodium ascorbate; strictly oxygen-controlled conditions often unnecessary but degassing can improve consistency.
SPAAC (copper-free with DBCO/BCN): purely aqueous buffers (PBS) or mixed aqueous-organic media (e.g., PBS/DMSO) enable bioconjugations.
Alcohol derivatization (tosylation/mesylation, carbonate formation): use dry dichloromethane, THF, MeCN, or DMF with mild base (e.g., Et3N, pyridine) under anhydrous conditions.
Comparison notes (literature)
Versus longer PEG-azides: lower viscosity and higher reactivity in organic media; slightly reduced aqueous solubility.
Versus 2-azidoethanol: improved water compatibility and lower volatility; slightly bulkier linker which can influence steric environment in coupling.
Confirm the supplied solution solvent before planning extractions or solvent switches to avoid precipitation or concentration of the azide.
Storage and Reconstitution
Item-specific storage/shipping
Storage: Store at 2–8 °C (as provided in Product Data).
Shipped: On wet ice.
Handling the solution
Keep tightly closed, in the original container, protected from light and heat. Record the receipt date and minimize headspace opening to limit solvent loss or contamination.
Concentration and solvent: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution/use
Supplied as a ready-to-use solution; no reconstitution typically required. Mix gently before use to ensure homogeneity.
If crystallization or phase separation is observed upon cold storage, allow to warm to room temperature and vortex to redissolve. If insoluble material persists, verify solvent identity and concentration on the CoA.
For precise stoichiometry in reactions, determine the exact concentration (by CoA or titration/quantitative NMR) before use.
Stability guidance
Avoid prolonged exposure to elevated temperature. Do not concentrate to dryness; avoid rotary evaporation to complete dryness due to azide safety considerations.
Store away from acids, strong oxidants, and reactive metals. Use clean, dry tools; reseal promptly after dispensing.
Research use note: For research use only.
Structure and Identity
Brief overview: 2-[2-(2-Azidoethoxy)ethoxy]ethanol solution is a short PEG-like azido alcohol bearing a terminal azide (–N3) and a terminal primary alcohol (–CH2OH) connected by a triethylene glycol spacer. This bifunctional motif is widely used as a hydrophilic linker and azide handle for click chemistry.
2D structural description (literature): A linear chain of three –CH2–CH2– units interrupted by two oxygens (–O–CH2–CH2–O–), terminating in a primary alcohol at one end and a linear azide (–N=N+=N−) attached to a terminal methylene at the other. No rings, no stereocenters, and no geometric isomerism.
Synthetic Utility
This reagent offers two orthogonal functional handles:
Azide (–N3) reactivity (literature)
Click cycloadditions: CuAAC with terminal alkynes; SPAAC with strained cyclooctynes to give triazoles with excellent chemoselectivity.
Staudinger reduction/ligation: PPh3-mediated conversion to a primary amine (after hydrolysis) or ligation to phosphine esters to form amide-like linkages under mild conditions.
Alcohol (–CH2OH) reactivity (literature)
Activation as sulfonates (Ms/Ts) or carbonates to enable SN2 substitution, polymer grafting, or surface immobilization.
Oxidation to aldehyde/acid for further coupling (Schiff base formation, reductive amination, amide coupling after oxidation).
Esterification/urethane formation to install protecting groups or functional anchors.
Spacer attributes
The triethylene glycol-like segment imparts flexibility, increases water compatibility, and helps separate functional groups from surfaces or biomolecular recognition sites, often improving accessibility in conjugation chemistry.
Orthogonality strategy
Sequence alcohol chemistry first (under azide-stable conditions), then perform click; alternatively, click first and derivatize the alcohol if the triazole is compatible with the conditions.
Plan conditions to preserve azide integrity: avoid strong acids, nitrosating conditions, and high-temperature operations; do not distill to dryness.
Target Specificity
Not applicable. This product is a small-molecule reagent (azido alcohol) and is not an antibody, enzyme, or affinity reagent. No antigen or biological target specificity is associated with the catalog item.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
![2-[2-(2-Azidoethoxy)ethoxy]ethanol solution - ~0.5M in tert-butyl methyl ether , CAS No.86520-52-7](https://www.aladdinsci.com/media/catalog/product/placeholder/default/default_4.jpg)