This compound belongs to the class of organic compounds known as methoxyanilines. These are organic compound containing an aniline group substituted at one or more positions by a methoxy group.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Punto de inflamación (°F)
-22 °F
Punto de inflamación (°C)
-30 °C
Peso molecular
149.150 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
149.059 Da
Monoisotopic Mass
149.059 Da
Topological Polar Surface Area
23.600 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
157.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calculadoras de soluciones
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Application Protocols
Item-specific tested application protocols are not provided for this product.
General guidance (informational only; adapt to your system)
CuAAC small-molecule coupling (micro-scale):
Dissolve alkyne partner (1.0 equiv) and 4-azidoanisole (1.1 equiv) in t-BuOH/H2O (1:1) to 10–50 mM total. Add CuSO4·5H2O (5 mol%) and sodium ascorbate (10 mol%). Optionally, add TBTA (10 mol%). Stir at 25–40°C for 4–16 h. Monitor by LC–MS/TLC. Extract with EtOAc, wash, dry, and purify.
In dry THF at 0–25°C, combine 4-azidoanisole (1.0 equiv) with PPh3 (1.2 equiv). After formation of iminophosphorane, add water or MeOH and stir to hydrolyze to the aniline. Remove PPh3O by filtration or chromatography.
Photolysis/nitrene insertion:
Prepare a degassed solution in MeCN with excess alkene trap. Irradiate at 365 nm under cooling with an LED source, monitoring by LC–MS. Quench light and proceed to workup under low light.
Note: These are generalized literature-style procedures and are not validated for this specific catalog item. Verify concentration/solvent of the supplied solution from the CoA before use and perform small-scale trials.
Biological Roles
Item-specific biological/clinical roles: Not applicable to this catalog item; for research use only.
Literature/general context
Aryl azides are not natural metabolites. However, 4-azidoanisole serves as a versatile photoreactive probe precursor in chemical biology. Upon UV activation, the aryl nitrene inserts into proximal C–H/N–H bonds, enabling covalent capture of interacting biomolecules in vitro or in cell lysates (subject to institutional approvals and safety controls).
As an azide, it can also be incorporated into bioconjugation schemes via CuAAC to append reporter tags (fluorophores, biotin) to alkyne-bearing targets. The para-methoxy group can modulate electronic properties, potentially affecting photolysis rates and site selectivity of nitrene reactions.
No endogenous biochemical pathway utilizes aryl azides, and they should be treated as xenobiotic research reagents. Any biological experimentation should be designed to control for phototoxicity and off-target nitrene reactions.
Good practices
Use minimal effective concentrations; validate labeling specificity with dark controls and azide-free controls.
For protein/peptide work, degas buffers if nitrene lifetimes are being probed, and quench residual copper post-CuAAC to protect biomolecules (e.g., with EDTA).
Strictly avoid implying therapeutic utility; this reagent is a discovery tool only.
Buffer Applications
Not typically applicable.
4-Azidoanisole is a hydrophobic aryl azide; it is not a buffering agent and does not form defined buffer systems. For experiments involving this reagent in aqueous media (e.g., CuAAC bioconjugation), select an appropriate external buffer (e.g., phosphate, HEPES, or Tris) compatible with copper catalysis and photochemistry.
Practical tip (general): Avoid strong bases that may accelerate undesired decomposition. For CuAAC, pH ~7–8 phosphate or HEPES buffers with added co-solvent (DMSO, t-BuOH, or ethanol) are common. Always confirm compatibility with your specific substrates.
Green Alternatives
Context
The functional group (aryl azide) is inherently energetic and photolabile; greening focuses on solvent choice, energy input, and minimizing halogenated waste rather than replacing the azide when that reactivity is required.
Greener solvent options (literature/general)
Consider 2-MeTHF, ethanol, or acetonitrile in place of dichloromethane or benzene for photolysis and coupling steps, balancing solubility and photochemical transparency.
For CuAAC, aqueous ethanol or t-BuOH/H2O mixtures reduce reliance on DMF/DMSO; use water-soluble ligands to keep copper homogeneous.
Small comparison (general)
DCM: excellent solubility/phototransparency; high EHS burden.
Acetonitrile: polar aprotic, good for photolysis; better EHS profile than DCM; recyclable.
2-MeTHF: bio-based, lower peroxide propensity than THF, good for extractions and some photoreactions; immiscible with water.
Ethanol/water: renewable, benign; may limit solubility of hydrophobic partners but ideal for CuAAC with suitable ligands.
Process considerations
Energy: Use LEDs (365–405 nm) instead of mercury lamps to improve efficiency and reduce hazardous UV where compatible with reactivity.
Catalysts: Employ ligand-accelerated CuAAC to lower copper loading and facilitate aqueous media; recover copper via scavengers.
Waste: Segregate azide-containing and copper-containing waste; implement solvent distillation/reuse where permissible.
Tradeoffs
Greener solvents can change nitrene selectivity and CuAAC rates; run small trials to confirm parity with legacy solvents.
Pharmaceutical Uses
Not a formulated drug substance or excipient (no clinical claims).
Literature/general formulation and process context
In discovery and preclinical research, aryl azide functionality is employed in photoaffinity probe design to map protein–ligand interactions via UV-induced covalent capture. 4-Azidoanisole can serve as a synthetic intermediate en route to such probes (e.g., incorporated into scaffolds that later receive reporter handles by CuAAC).
Manufacturing/process relevance: None established for approved pharmaceuticals. If used in process development as an intermediate, ensure proper purge of residual azide and photolysis byproducts, and validate that no inorganic azides form.
Regulatory: Not a compendial excipient. Any use in GMP settings would require project-specific specifications, validated analytical methods (e.g., HPLC/LC–MS for azide content), and robust safety assessments for energetic functional groups.
Physical Properties
Item-specific specs
Appearance, concentration, solvent, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for neat 4-azidoanisole (informational, not product specifications)
Phase/appearance: Often reported as a pale yellow liquid or low-melting solid; aryl azides can show light sensitivity.
Thermal behavior: Aryl azides decompose on heating and on UV irradiation to form nitrenes; avoid distillation to dryness and strong heating.
Solubility: Sparingly soluble in water; soluble in common organic solvents (e.g., acetonitrile, dichloromethane, THF, toluene, ethers, alcohols) — literature/general.
Density, bp/mp, refractive index, UV cutoff: Not widely standardized for this specific aryl azide; values can vary by source; consult primary literature or CoA/SDS for exact data.
Partitioning: Expected to be moderately lipophilic due to anisole core, with increased polarity from the azide (qualitative literature expectation).
Practical notes for handling solutions (general)
Photolabile: Use amber vials and minimize ambient/UV light exposure.
Headspace/inerting: Store with minimal headspace and consider inert atmosphere to limit oxidative pathways, especially if the solvent is air-sensitive.
Peroxide concern: The azide itself does not form peroxides, but common ether solvents might; test and remediate peroxides in ether media per institutional policy.
Quality and Grades
Item-specific grade/purity and stabilizer information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/solvent system: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for professional use
When a “solution” of an energetic functional group (aryl azide) is supplied, vendors often standardize concentration for safer handling and predictable stoichiometry. In the absence of an indicated grade, confirm assay/concentration by CoA or by independent titration/NMR integration if critical to yield calculations.
Chromatography suitability: If using for CuAAC or photolysis product synthesis destined for analytical work, assess UV background and impurity content of the solvent matrix (e.g., HPLC/GC baseline); HPLC or LC–MS-grade solvents minimize background.
Light stabilization: Commercial aryl azide solutions may be packaged in amber containers. If long-term storage is needed, verify presence/absence of stabilizers (e.g., radical inhibitors) on the CoA to anticipate downstream purification.
Trace metals: For click chemistry, low copper background prior to catalysis is preferred. If metal content is critical, request elemental analysis from the CoA.
Batch verification: For reproducibility, verify concentration by quantitative 1H NMR against an internal standard, or UV assay if an extinction coefficient is known (literature-dependent).
Reaction and Applications
Scope (literature/general for 4-azidoanisole; expand beyond catalog line)
Photochemistry to nitrenes: Upon UV irradiation (typically 254–365 nm), aryl azides expel N2 to form singlet aryl nitrenes which undergo insertion (C–H, N–H), addition to alkenes (aziridination), ring expansion to dehydroazepines, or rearrangements. Para-methoxy substituent can modulate nitrene lifetimes and selectivity.
Click chemistry (CuAAC): Reacts with terminal alkynes under Cu(I) catalysis to give 1,4-disubstituted triazoles. Aryl azides are less reactive than alkyl azides but proceed efficiently with proper ligands (e.g., TBTA/THPTA) and catalytic systems (CuSO4/ascorbate or CuBr/ligand).
Staudinger reaction/reduction: With phosphines (e.g., PPh3) to give iminophosphoranes; hydrolysis affords 4-aminoanisole (p-anisidine) derivatives. This is a useful route to para-anilines without harsh nitro reductions.
Transition-metal-mediated transformations: Aryl azides can participate in metal-catalyzed amination/amination–carbonylation manifolds after nitrene transfer from the azide (e.g., Rh, Cu, Fe systems), enabling C–H amination.
Photoaffinity labeling precursor: The aryl azide group serves as a photoreactive handle for covalent capture in chemical biology workflows (non-clinical, discovery-stage applications).
Practical tips
Light management: For storage and routine handling, exclude light; expose only during controlled photoreactions.
Degassing: For photolysis aimed at nitrene trapping, degas to reduce quenching by oxygen; use N2 or Ar sparging.
Copper handling: For CuAAC, ensure proper ligand and copper source to accelerate otherwise sluggish aryl azide cycloadditions; maintain reducing environment to generate Cu(I) in situ.
Monitoring: Use TLC or LC–MS; azides show characteristic IR N3 stretch around 2100 cm−1 (literature) which disappears on conversion.
Reaction Conditions
General literature guidance (not product specifications)
CuAAC (aryl azide + terminal alkyne):
Catalyst: CuSO4·5H2O (1–10 mol%) + sodium ascorbate (reducing agent) to generate Cu(I) in situ; or CuBr/CuI (5–10 mol%) with ligands (e.g., TBTA, THPTA 5–20 mol%).
Solvent: t-BuOH/H2O (1:1), EtOH/H2O, DMSO/H2O, or MeCN/H2O.
Temperature: 20–50°C; time: 2–24 h depending on substrates/ligand.
Notes: Aryl azides benefit from higher ligand loading and sometimes elevated temperature for complete conversion. Degas to limit oxidative side reactions.
Staudinger reduction (to aniline):
Reagents: Triphenylphosphine (1.1–1.5 equiv), THF or toluene; add H2O or MeOH for hydrolysis of iminophosphorane.
Temperature: 0–25°C; time: 0.5–6 h.
Workup: Oxidize or precipitate triphenylphosphine oxide; silica plug may retain byproduct.
Photolysis to nitrene:
Light source: 254–365 nm UV; LEDs at 365–405 nm may be used depending on required excitation.
Solvent: MeCN, toluene, DCM; rigorously exclude light until irradiation begins; consider cryogenic or room-temperature conditions depending on selectivity.
Trapping: Alkenes (aziridination), sulfides/amines (insertion), or intramolecular rearrangement targets.
Notes: Degas (N2/Ar), control intensity to manage exotherm; employ quartzware for <300 nm.
Yields
Highly substrate- and setup-dependent. Aryl azide CuAAC commonly affords good to excellent yields with proper ligation; photolysis outcomes vary widely with trapping partner and wavelength. Consult primary literature for closely related substrates.
Safety overlay
Scale cautiously. Maintain dilution, cooling, and shielding for photolysis. Avoid concentrating to dryness.
Safety and Handling
Item-specific hazard fields from Product Data
GHS Classification, pictograms, signal word, and H-statements: Not specified for this item; refer to SDS.
General safety information for aryl azides and their solutions (informational; defer to SDS for authoritative guidance)
Hazards: Aryl azides are photosensitive and thermally labile, releasing nitrogen to form reactive nitrenes. May cause skin/eye irritation. Combustible solvents may be present in the solution (solvent not specified). Avoid heat, shock, and strong UV sources.
Photoreactivity: Protect from light; use amber glass and foil wrap. Avoid concentrated irradiation unless intended for reaction.
Incompatibilities: Avoid contact with strong reducing agents and strong acids/bases that may accelerate decomposition; avoid heavy metals and metal salts which can catalyze side reactions. Keep away from ignition sources.
PPE: Use lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles. Work in a fume hood.
First aid (overview): In case of skin contact, wash with soap and water. For eye exposure, rinse for ≥15 minutes and seek medical attention. If inhaled, move to fresh air; if swallowed, seek medical attention. Always follow site-specific SOPs and SDS.
Spill/cleanup: Absorb small spills with inert material while minimizing light exposure. For solutions in volatile organics, control ignition sources and ventilate. Collect in light-protected waste.
Waste: Collect azide-containing waste separately; do not allow contact with lead or copper plumbing. Label as “organic azide-containing waste.”
Transport internal to facility: Use secondary containment; keep cold as supplied.
Solvent Selection
Applicability
This product is supplied as a solution (solvent not specified). Selection of reaction medium should consider the reactivity of aryl azides (photolysis to nitrenes; participation in CuAAC) and the solubility of substrates.
Polarity and miscibility (literature/general for aryl azides)
Aryl azides dissolve well in moderately polar aprotic solvents (acetonitrile, DMF, DMSO), chlorinated solvents (DCM, chloroform), and aromatic/ether solvents (toluene, THF). Water solubility is low, but CuAAC often proceeds in mixed aqueous–organic systems.
Typical medium choices by application
Photolysis/nitrene chemistry: Acetonitrile, toluene, or dichloromethane; degassed if trapping singlets; use transparent vessels and control wavelength (254–365 nm).
CuAAC (click chemistry): t-BuOH/H2O, ethanol/H2O, or DMSO/H2O mixtures with Cu(I) sources; add ligands (e.g., TBTA/THPTA) to solubilize copper and enhance kinetics.
Staudinger reductions: THF, THF/H2O, or toluene; triphenylphosphine or water-soluble phosphines depending on medium.
Comparison notes (literature/general)
Acetonitrile vs DCM: MeCN is polar, supports photolysis control and green(er) profile; DCM offers excellent solubility but is halogenated and less preferred environmentally.
THF vs 2-MeTHF: 2-MeTHF offers improved sustainability and sometimes higher photochemical quantum yields due to reduced peroxide formation and different polarity.
Caveats
Avoid strongly basic aqueous media that can accelerate undesired decomposition. Protect solutions from light irrespective of solvent choice.
Storage and Reconstitution
Item-specific instructions (from Product Data)
Storage: Store at -20°C.
Shipping: Ice chest + ice pads (keep cold on receipt).
Additional best practices for this compound class and format
Light protection: Store in amber vials or wrap in foil. Minimize exposure to ambient and UV light.
Headspace and atmosphere: Keep containers tightly closed; consider inert gas blanket (N2/Ar) if repeatedly opened.
Freeze–thaw: If the solvent freezes at –20°C, minimize freeze–thaw cycles by aliquoting upon receipt. Verify solvent identity and freezing point on CoA.
Compatibility: Avoid contact with metals and metal salts during storage. Use PTFE-lined caps.
Stability: Aryl azides can slowly degrade under light/heat. Maintain cold, dark storage to maximize shelf life.
Reconstitution
Not applicable: This item is supplied as a solution. If concentration adjustment is required, dilute under low-light conditions with a solvent compatible with your application (e.g., MeCN, THF, t-BuOH) after confirming the original solvent and assay from the CoA/Spec Sheet.
Labeling and documentation
Record receipt date, lot number, and any aliquoting/dilution performed. Consult the SDS for definitive stability and handling guidance before first use.
Structure and Identity
Item-specific facts (from Product Data)
Product: 4-Azidoanisole solution (SKU A462929)
CAS: 2101-87-3
Storage: Store at -20°C
Shipment: Ice chest + ice pads
Research use: For research use only
InChIKey (as provided): 283581 (note: this is not in the standard 27-character InChIKey form; consult CoA/SDS for definitive identifier)
Literature/computed identifiers and structural description (for the neat compound 4-azidoanisole; informational)
Core structural features: An anisole ring (methoxy-substituted benzene) bearing a para-azido substituent. Functional groups include an aryl ether (–O–CH3) and an aryl azide (–N3). The ring is para-disubstituted, giving a 1,4-disposition of –OCH3 and –N3. No stereocenters; planar aromatic system.
2D description in words: A benzene ring with a methoxy group at position 1 and an azido group at position 4 (para). The azide is linear (–N=N+=N– resonance) attached directly to the aromatic carbon; the methoxy group is bound through oxygen to a methyl substituent.
Notes
The product is supplied as a solution; solvent, concentration, and stabilizers are Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional group leverage (literature/general)
Aryl azide as masked nitrene: UV or thermolysis generates nitrenes capable of intramolecular rearrangements and intermolecular insertion, enabling synthesis of aziridines, anilides (via rearrangement), and seven-membered dehydroazepines.
Azide-to-amine conversion: Staudinger reduction (PPh3/H2O or polymer-supported phosphines) to yield para-anilines (e.g., p-anisidine), providing a mild alternative to nitro reductions.
Triazole formation: Cu(I)-catalyzed cycloaddition with terminal alkynes affords 1,4-disubstituted triazoles, a robust bond-forming step in linker chemistry and materials science. Aryl azides often benefit from ligand-accelerated conditions.
Electrophilic amination: In presence of transition metals (Rh, Cu, Fe, Co), aryl azides act as nitrene precursors for C–H amination or aziridination of alkenes/allenes, useful in late-stage functionalization.
Strategic points
Para-methoxy group tunes electronics (donating), which can influence nitrene spin state equilibria and regioselectivity in insertions/rearrangements; it also provides a handle for further modifications (e.g., demethylation to phenol, ether cleavage for diversification).
Orthogonal chemistry: Azide is orthogonal to many protecting groups and can survive mild acid/base; avoid prolonged exposure to strong nucleophiles or reducing agents unless intentional.
Analysis: Monitor azide consumption by IR (νN3 ~2100 cm−1), LC–MS (loss of 28 amu on nitrene formation), or 1H NMR (disappearance of azide-adjacent aromatic resonances upon transformation).
Target Specificity
Not applicable.
This product is a small-molecule aryl azide solution, not an antibody or biological targeting reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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