This compound belongs to the class of organic compounds known as phenylazides. These are compounds containing a phenylazide moiety, which consists of a linear azide substituent attached to a phenyl 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.
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Application Protocols
No application protocols are provided for this item. For general use, consult standard procedures for:
Staudinger reduction of aryl azides to anilines.
Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) for aryl azides.
Photolysis of aryl azides for nitrene insertion/crosslinking.
Optimize solvent, concentration, and light/catalyst conditions based on your substrate and refer to the CoA/SDS for handling guidance.
Biological Roles
This product is a small-molecule aryl azide reagent supplied as a solution and is intended for research use only.
General context (literature)
Aryl azides have been widely used as photoaffinity probes: upon UV activation they generate nitrenes that insert into proximal C–H, N–H, or O–H bonds, enabling covalent capture of binding partners in biochemical systems.
The azide group also participates in bioorthogonal azide–alkyne cycloadditions to form triazoles; aryl azides are less reactive than alkyl azides under uncatalyzed conditions, so Cu(I) catalysis or strain-promoted systems are typically required.
Not a biological metabolite
2-Azidotoluene is not known as a natural metabolite or cofactor. Its biological utility stems from its reactivity rather than intrinsic biological function.
Experimental cautions
Photolysis in biological matrices should account for light scattering, oxygen quenching, and potential off-target insertions.
Copper used in CuAAC can be cytotoxic; appropriate chelation and removal are required for downstream applications.
No medical or clinical claims are made for this product.
Buffer Applications
This is a hydrophobic aryl-azide reagent supplied as a solution; it is not a buffering agent and is not used to control pH. For applications involving this reagent in aqueous systems (e.g., CuAAC), select standard biological buffers (e.g., PBS, HEPES) compatible with copper catalysis and organic co-solvents, while protecting the azide from light.
For photolysis/nitrene chemistry, consider CPME or 2-MeTHF instead of dichloromethane or acetonitrile when compatible with light transmission and substrate solubility.
For CuAAC, aqueous ethanol or t-BuOH/H2O mixtures reduce reliance on chlorinated solvents; heterogeneous copper catalysts on recyclable supports can simplify metal removal.
Reagent/design considerations
If the end goal is an aniline, alternative reductions (e.g., catalytic hydrogenation of nitro precursors) may avoid azide handling, depending on functional-group tolerance.
For triazole formation in sensitive settings, organic azides can be generated in situ from anilines via diazotization/azidation, minimizing isolation; flow chemistry can also improve safety.
Comparison snapshot (general; not item specifications)
DCM vs CPME: DCM offers excellent UV transparency but is chlorinated and volatile; CPME has better environmental profile, higher boiling point, and lower peroxide formation than many ethers, with acceptable UV transmission for 300–365 nm work.
MeCN vs 2-MeTHF: MeCN is polar and efficient for CuAAC; 2-MeTHF is bio-derived and less hazardous but less polar—may require co-solvent or elevated temperature.
Safety-driven green practice
Keep azide concentrations low, avoid accumulation of energetic residues, and implement in-line quenching or continuous processing when feasible.
Pharmaceutical Uses
This catalog item is a research reagent (aryl azide solution) and is not an excipient or dosage-form component.
General formulation context (literature/general)
Aryl azides can serve as synthetic intermediates toward anilines, triazoles, or photo-crosslinked scaffolds used in medicinal chemistry discovery. They are typically consumed in synthesis and not present in final drug products.
Due to energetic and toxicological concerns, neat azides are rarely used in pharmaceutical manufacturing without rigorous hazard assessment; solution delivery, low-temperature storage, and flow chemistry are common risk mitigations.
No pharmacopeial monograph or excipient status is implied for this item.
Physical Properties
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage/Shipping (from Product Data)
Storage: Store at −20 °C
Shipped in: Ice chest + ice pads
Literature/General physicochemical information (for reference; not item specifications)
Phase: typically a liquid aryl azide at ambient conditions when neat; supplied here as a solution.
Functional groups: aryl azide (energetic, nitrene precursor); methyl on aromatic ring (weakly activating).
Polarity: low-to-moderate; expected to be soluble in common organic solvents (e.g., dichloromethane, acetonitrile, THF, toluene) and poorly soluble in water (literature/general).
Thermal behavior: aryl azides can decompose exothermically upon heating; photolysis occurs under UV (254–365 nm) to generate aryl nitrenes (literature).
Typical stability: more thermally and shock stable than alkyl or acyl azides, but still sensitive to light and heat; avoid concentration to dryness without risk assessment (literature/practice).
Values not provided for this catalog item
Boiling point, melting point, density, refractive index, UV cutoff, logP, pKa, water content, metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Quality & Grades
Item-specific status
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance)
For azide building blocks supplied as solutions, grade typically reflects control of purity of the aryl azide component (by GC/LC, NMR) and the solvent quality (water/peroxide/UV background) suitable for reaction development or photolysis studies. In absence of a stated grade, consult the CoA for assay, solvent identity, and impurity profile.
Considerations specific to aryl-azide solutions (general)
UV background: For photochemical applications, low-UV solvents reduce baseline absorbance; HPLC-grade or “UV-cut” solvents are preferred when applicable.
Metal content: Trace metals can catalyze side reactions (e.g., CuAAC) unintentionally; if this is a concern, request metal screening data or re-filter through metal-free hardware.
Stabilization: Some suppliers include light stabilizers or deliver under inert gas; verify presence/absence on the CoA to plan workups and photolysis conditions.
Documentation
For batch-specific assay, residual solvents, water content, and any stabilizer: Not specified for this item; refer to CoA/Spec Sheet.
Reaction & Applications
General utility of 2-azidotoluene (literature/practice)
Nitrene precursor: UV or thermal activation expels N2 to generate an o-tolyl nitrene that can undergo C–H insertion, rearrangement, aziridination of alkenes, or ring expansion. Photolysis wavelengths 254–365 nm are commonly used; inert, dilute conditions minimize side reactions.
Staudinger reduction: Treatment with triphenylphosphine (or other phosphines) forms an iminophosphorane that hydrolyzes to o-toluidine. Mild, chemoselective route to anilines in complex settings.
Azide–alkyne cycloaddition: Forms 1,2,3-triazoles via thermal (Huisgen) or Cu(I)-catalyzed (CuAAC) pathways. Aryl azides generally require catalysis; CuAAC with CuSO4/Na ascorbate, or CuBr/ligand, is standard.
Photoaffinity labeling precursor: Aryl azides are classic photo-crosslinkers; upon irradiation they form nitrenes that insert into proximal bonds. 2-Substitution can influence nitrene rearrangement pathways.
Practical tips (general)
Exclude oxygen and moisture where feasible during photolysis; oxygen quenches excited states.
Use quartz or UV-transparent glassware for wavelengths <320 nm; calibrate lamp intensity and distance.
Keep concentrations low (e.g., 1–10 mM) for photochemistry to improve light penetration and control heat.
For CuAAC with aryl azides, consider Cu(I) sources with stabilizing ligands (TBTA, THPTA) to enhance rates and suppress side reactions; gentle heating (30–60 °C) may be beneficial.
Workup often requires careful removal of residual phosphine oxide (Staudinger) or copper (CuAAC) by chelation/resin.
Reaction Conditions
The following are general literature conditions for aryl azides and should be adapted to your substrate and this specific solution formulation.
Staudinger reduction to o-toluidine (literature)
Reagents: 1.1–1.5 equiv PPh3 in THF, toluene, or MeCN; add H2O or aqueous workup.
Conditions: 20–25 °C, 0.05–0.2 M; several hours until azide consumption by TLC/IR (loss of ~2100 cm−1 band).
Notes: Avoid strong acids/bases; remove Ph3P=O by filtration or chromatography.
Solvent: t-BuOH/H2O (1:1) or MeCN/H2O; 0.05–0.2 M.
Temp/time: rt to 60 °C, 2–24 h. Aryl azides may require longer times or elevated temperature.
Workup: Chelate copper (EDTA/bipy), then extract; pass through metal-scavenging resin if needed.
Photolysis/nitrene chemistry (literature)
Light source: 300–365 nm (medium-pressure Hg lamp or LEDs); quartzware for <320 nm.
Solvent: toluene, DCM, CPME, or acetonitrile; 0.001–0.01 M to enhance light penetration.
Atmosphere: N2 or Ar; cool to manage exotherm.
Notes: Monitor by UV–vis or GC/MS; protect operators from UV; use appropriate shielding.
Safety integration
Keep total azide inventory minimal; avoid concentrating to dryness; ensure blast shielding for photolysis on scale.
Safety & Handling
Item-specific hazard information (from Product Data)
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 hazards of aryl azides (literature/practice; consult SDS for authoritative guidance)
Sensitivity: Aryl azides can be photosensitive and may decompose exothermically upon heating to form reactive nitrenes; avoid UV exposure and elevated temperatures.
Incompatibilities: Avoid contact with strong reducing agents; strong acids/bases that can induce decomposition; and heavy-metal salts/surfaces (Cu, Pb, Ag) that can form highly sensitive metal azides. Minimize friction/shock for any residue.
Toxicology: Harmful if inhaled/ingested; may cause skin/eye irritation. Decomposition can release nitrogen and potentially hazardous byproducts.
Handling and PPE (best practice)
Work in a fume hood; protect from light (amber glass/aluminum foil).
Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles; for scale-up or photolysis operations, consider face shield and cut-resistant gloves.
Use inert, non-metallic tools/needles when practical; avoid copper/brass syringes or needles.
Keep solutions dilute; avoid concentrating to dryness without a documented hazard assessment.
First-aid (overview; defer to SDS)
Inhalation: move to fresh air; seek medical attention.
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
Fire: use CO2, dry chemical, or foam; cool containers; decomposition may intensify fire.
Storage (from Product Data + best practice)
Store at −20 °C in tightly closed, light-protective containers; segregate from acids/bases and metals; maintain secondary containment. Shipments are provided cold to limit decomposition.
Solvent Selection
Because this product is itself supplied as a solution, the choice of additional solvent depends on your transformation. The native solvent and concentration are Not specified for this item; refer to CoA/Spec Sheet.
Polarity and miscibility (literature/general for aryl azides)
Common compatible solvents: acetonitrile, dichloromethane, THF, ethyl acetate, toluene. Water immiscibility is typical; mixed aqueous–organic systems are used for CuAAC.
Dielectric/polarity effects: Polar aprotic solvents (MeCN, DMF, DMSO) can accelerate Huisgen cycloadditions; nonpolar aromatics (toluene) are often preferred for photolysis/nitrene chemistry to limit side reactions.
When to choose what
Photolysis/nitrene insertions: toluene, dichloromethane, or cycloalkyl ethers (e.g., CPME) to moderate energy transfer and solubilize aromatic substrates; deoxygenate to suppress quenching.
Staudinger reductions: THF, toluene, or MeCN with PPh3; aqueous workup to reveal anilines.
CuAAC (triazole formation): t-BuOH/H2O or MeOH/H2O with CuSO4/ascorbate or preformed Cu(I); aryl azides are less reactive than alkyl azides—use catalysts/ligands accordingly.
Practical notes
Avoid copper/brass wetted parts unless intentionally catalyzing CuAAC.
Protect solutions from light regardless of solvent; use amberware.
If switching solvent, gently concentrate under reduced light and low temperature; avoid going to dryness without risk assessment.
Storage & Reconstitution
Item-specific storage (from Product Data)
Store at −20 °C.
Shipped in an ice chest with ice pads.
Handling and storage best practices (general for aryl-azide solutions)
Protect from light at all times (amber vials, foil wrap); minimize freeze–thaw cycles by aliquoting upon receipt.
Store tightly sealed under inert gas if possible to limit oxidation or adventitious metal contamination. Secondary containment is recommended.
Avoid contact with copper/lead/other heavy metals that may form sensitive metal azides.
Reconstitution
The product is supplied as a solution; no reconstitution is required. If solvent exchange or dilution is needed, perform at low temperature, under subdued light, and avoid concentrating to dryness.
Stability
Shelf-life, concentration, and any stabilizer are Not specified for this item; refer to CoA/Spec Sheet. Inspect periodically (e.g., NMR/IR) if storing long-term to confirm integrity (loss of azide IR band near ~2100 cm−1 indicates consumption).
Structure & Identity
Brief overview: 2-Azidotoluene is an ortho-methyl–substituted aryl azide supplied as a solution. The aryl azide functionality (–N3) on a toluene ring enables photolytic or thermal nitrene chemistry and Staudinger reduction to anilines.
Item-specific (from Product Data)
SKU: A462933
Product name: 2-Azidotoluene solution
CAS: 31656-92-5
PubChem CID: 141652
InChIKey: 459313
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/General identity (for reference; not item specifications)
Core structural features: benzene ring bearing an azido group (–N3) ortho to a methyl group (–CH3). The azido group is linear (–N=N+=N− resonance forms) and acts as a nitrene precursor.
2D description in words: a six-membered aromatic ring with adjacent substituents at positions 1 (azido) and 2 (methyl). No stereocenters; planar aryl core.
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)
Azide → Aniline: Staudinger reduction (PPh3/H2O) or catalytic hydrogenation affords o-toluidine derivatives with high chemoselectivity.
Azide → Nitrene chemistry: Photolysis/thermolysis generates aryl nitrenes that undergo insertions, rearrangements (to azepines or ring expansion products), or C–H amination.
Retrosynthetic value
2-Azidotoluene is a versatile masked amine synthon at the ortho position; it allows late-stage installation of an aniline without strongly basic or nucleophilic conditions.
Orthogonal reactivity: The azide group tolerates many conditions (e.g., some cross-couplings on other sites) and can be unveiled under mild conditions later in a sequence.
Practical synthetic notes
Maintain dilute conditions for photochemistry to manage heat and light penetration.
For Staudinger, removal of Ph3P=O by precipitation or adsorption (e.g., silica, fluorous-tag strategies) simplifies purification.
For CuAAC with aryl azides, use efficient Cu(I) sources and ligands (e.g., TBTA/THPTA) to overcome lower intrinsic reactivity relative to alkyl azides.
Target Specificity
Not applicable. This product is a small-molecule aryl azide solution and is not an antibody, enzyme, or biologic. No target, epitope, or species specificity applies.
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