p-Nitrobenzazide , CAS No.17271-88-4

CAS: 17271-88-4 Cat. No.: P1020345 Formula: C₇H₆N₄O₂ Peso molecolare: 178.150

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: C1=CC(=CC=C1CN=[N+]=[N-])[N+](=O)[O-]
• IUPAC Name: 1-(azidomethyl)-4-nitrobenzene
• InChIKey: CBJPXFJWGZHREB-UHFFFAOYSA-N
• INCHI: 1S/C7H6N4O2/c8-10-9-5-6-1-3-7(4-2-6)11(12)13/h1-4H,5H2
• Peso molecolare: 178.150

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Nitroaromatic compounds Azo imides Azo compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Azo compound - Azo imide - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Organic salt - Organic cation - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 178.150 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 178.049 Da
• Monoisotopic Mass: 178.049 Da
• Topological Polar Surface Area: 60.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 223.000
• 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

Application Protocols

Item-specific validated applications and protocols: Not specified for this item; refer to CoA/Spec Sheet.

General starting points (verify structure and compatibility first):

• Photoaffinity labeling: Prepare a 1–10 mM stock in dry DMSO or MeCN; add to protein/lysate to 10–200 µM; irradiate at 302–365 nm on ice for 1–15 min; quench and analyze by SDS‑PAGE/MS. Shield controls from light.
• Curtius to carbamate: Dissolve substrate in dry toluene (0.05–0.2 M), heat to 90–110 °C with ROH (3–5 eq) and base (1–2 eq). Monitor gas evolution and IR (loss of νN3). Work up and purify by column chromatography.
• CuAAC: Combine azide (1.0 eq) and alkyne (1.2 eq) in t‑BuOH/H2O 1:1, add CuSO4 (5 mol%) and sodium ascorbate (10 mol%), stir at RT 2–6 h; extract and purify. For water-insoluble substrates, use MeCN/H2O or DMF.

These are general literature procedures and may require optimization. Conduct risk assessments before scaling.

Biological Roles

Item-specific biological roles: Not specified for this item; refer to CoA/Spec Sheet.

General context (not a medical claim):

• Aryl azides are widely used as photoreactive probes in chemical biology due to their ability to form nitrenes upon UV irradiation, enabling covalent capture of proximal biomolecules (photoaffinity labeling). Para‑nitro substitution can modulate absorption and reactivity, but biological compatibility depends on solubility, cytotoxicity, and activation wavelength.
• In bioorthogonal chemistry, azide groups participate in azide–alkyne cycloadditions (CuAAC and SPAAC). However, small aromatic azides may be too hydrophobic or cytotoxic for live-cell applications unless carried by a suitable scaffold.

Research use only: This product is intended strictly for research and laboratory use; no use in humans or diagnostics is implied.

Buffer Applications

This product is not a buffering agent and is not typically used to prepare biological buffers. If employed in biochemical assays (e.g., photoaffinity labeling or click reactions), it would be added as a reagent in an existing buffer system selected for the biology (PBS, HEPES, etc.). Choose buffers that do not absorb strongly at the photolysis wavelength and that lack nucleophiles if isocyanate intermediates are expected.

Green Alternatives

While the azide functionality is intrinsically energetic and warrants caution, greener choices can be made around solvent selection and process design (general guidance; not item-specific):

• Prefer lower-toxicity solvents:
  • Replace chlorinated solvents (DCM, chloroform) with safer options such as 2‑MeTHF, CPME, EtOAc, or toluene when compatible with kinetics and selectivity.
  • Use MeCN over DMF/DMSO where feasible for easier workup and lower EHS burden.
• Energy efficiency:
  • Curtius rearrangements can often proceed under flow conditions, improving heat transfer and reducing hold-up of energetic intermediates.
  • Photochemistry with LEDs (narrow-band, energy efficient) can reduce energy consumption compared to broad-spectrum lamps.
• Waste minimization:
  • Design telescoped sequences that capture isocyanates in situ to avoid isolation and extra solvent cycles.
  • Employ solid-supported scavengers to quench residual isocyanate or azide safely.

Trade-offs (general):

• Greener ethers (2‑MeTHF/CPME) can contain peroxides—implement routine testing and inhibitors as needed.
• Toluene/xylene offer higher boiling points for rearrangements but increase VOC load; balance against process intensification or flow.

Always confirm that alternative media do not promote undesired side reactions (e.g., solvent nitrene insertion or competing nucleophilicity).

Pharmaceutical Uses

No pharmacopeial/excipient status or formulation role is specified for this item; refer to CoA/Spec Sheet.

General manufacturing context (non-clinical):

• Aryl/acyl azides can serve as masked isocyanate precursors for the synthesis of ureas/carbamates, which are common motifs in APIs and intermediates. Such use occurs at the intermediate stage and not as a finished excipient.
• Due to energetic and toxicological concerns, process development typically favors in situ generation and consumption (telescoped Curtius) or continuous-flow handling to minimize inventory of the azide intermediate.

No therapeutic claims are made. For GMP or regulatory use, consult applicable guidance and perform comprehensive hazard and impurity assessments.

Physical Properties

Item-specific physico-chemical specifications (BP/MP/density/solubility/logP/refractive index): Not specified for this item; refer to CoA/Spec Sheet.

General literature context for para‑nitro–substituted aryl azides (informational, not item specifications):

• Physical state: typically crystalline solids or low-melting solids; strongly influenced by exact functionalization (aryl azide vs acyl azide).
• Solubility: many aryl azides are soluble in common organic solvents (EtOAc, DCM, THF, toluene, acetonitrile) and sparingly soluble in water; nitro substitution can decrease solubility in nonpolar media relative to unsubstituted analogs.
• Thermal behavior: acyl/aryl azides can be thermally or photochemically labile, evolving N2 to form nitrenes or undergoing Curtius-type rearrangements (general). Thermal stability depends heavily on substitution and matrix; avoid uncontrolled heating.
• UV-vis: aryl azides absorb in the near‑UV; para‑nitro substitution often red‑shifts and increases intensity (useful for photolysis), but exact λmax is structure-dependent.
• pKa/logP: not broadly applicable to neutral aryl azides; para‑nitro increases overall polarity vs phenyl azide (qualitative).

Use the item’s CoA for any numerical values (melting point, residual solvent, UV cutoff, metal limits, water/peroxide levels).

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Interpreting common grades (general guidance):

• Research/technical grade: suitable for routine synthesis; typical impurity controls without low-UV or trace-metal guarantees.
• High-purity/analytical grade: tighter specifications for assay and trace contaminants; often includes stabilizer and UV-absorbance limits (relevant to photochemistry or chromatography).
• HPLC/LC–MS grade (when applicable to solvents): low UV background and particulates; not typically relevant for solid azide reagents unless used as standards.

Stabilizers/inhibitors (general):

• Some azides are shipped with light-blocking packaging or under inert atmosphere to mitigate photolysis or oxidation; presence/absence of stabilizers should be checked on the specific CoA.

Batch documentation:

• For this SKU, defer to the lot-specific CoA for: assay, identity (NMR/IR/HRMS/HPLC), residual solvents, water (Karl Fischer), and any inhibitor/stabilizer content. Do not substitute generic literature values for specification-critical decisions.

Reaction and Applications

Manufacturer application text: Not provided. The following expands on common laboratory uses for para‑nitro–substituted aryl/acyl azides (general literature; verify applicability to this item’s exact structure before use):

• Curtius rearrangement (acyl azides): Thermal or photochemical conversion of acyl azides to isocyanates with loss of N2. The resulting isocyanate can be trapped by alcohols (urethanes/carbamates), amines (ureas), or water (amines via carbamic acid decarboxylation). Para‑nitro substitution can influence migration and stability of intermediates.
• Photolysis to nitrenes (aryl azides): UV irradiation generates singlet/triplet nitrenes that insert into C–H or add to π-systems; para‑nitro often stabilizes nitrene intermediates and modifies insertion selectivity.
• Click chemistry precursor: Aryl azides can undergo [3+2] cycloadditions with alkynes to form triazoles (thermally or catalyzed by Cu), enabling bioconjugation and surface modification workflows when solubility allows.
• Synthesis of 4‑nitroaniline derivatives: Via rearrangement/hydrolysis sequences or reduction/trapping pathways, providing access to para‑nitro–substituted ureas, carbamates, and anilines.
• Polymer modification and photoresists: Aryl azide photochemistry is used for crosslinking and patterning; para‑nitro groups tune absorption and reactivity.

Practical tips:

• Control temperature ramps carefully in rearrangements; use dilute solutions and vented apparatus to manage N2 evolution.
• Shield from strong light unless photolysis is intended. Validate structure-specific conditions on small scale before scale-up.

Reaction Conditions

Item-specific conditions are not provided; the following are general literature guidelines for aryl/acyl azide transformations. Confirm suitability for this exact compound on small scale.

• Curtius rearrangement (acyl azides):
  • Solvent: toluene, chlorobenzene, MeCN, or 1,2‑dichloroethane (dry).
  • Temperature: 70–140 °C depending on substrate; monitor for N2 evolution.
  • Traps: ROH (carbamate), RNH2 (urea), H2O (amine via carbamic acid), alcohols often used with base (Et3N, pyridine).
  • Time: 1–6 h typical; often complete once gas evolution ceases.
• Aryl azide photolysis:
  • Light source: 300–365 nm UV (or visible if sensitized); intensity and wavelength tune selectivity.
  • Solvent: inert, non-nucleophilic (toluene, MeCN, DCM); degas to reduce quenching.
  • Temperature: 0–25 °C for better control.
• Azide–alkyne cycloaddition (thermal):
  • Solvent: toluene, DMF, or DMSO; 60–120 °C.
  • Copper-catalyzed (CuAAC): CuSO4/sodium ascorbate or CuBr/ligand; 25–60 °C in t‑BuOH/H2O, MeOH/H2O, or MeCN; 0.5–12 h.

Workup tips:

• Quench residual isocyanates with MeOH or aqueous amine under controlled conditions.
• Remove copper with chelating resin or EDTA wash after CuAAC.
• Analyze by IR (νN3 ~2100 cm−1; disappearance indicates consumption) and by UV for photolysis progress.

Safety and Handling

GHS classification, signal word, pictograms, H‑statements (item-specific): Not specified for this item; refer to SDS.

General safety guidance for aromatic/acyl azides (literature-based; not item-specific):

• Hazards: Azides may be acutely toxic and can decompose exothermically to release nitrogen; some dry azides present energetic (explosive) risk, especially upon heating, friction, or shock. Aromatic azides are typically less impact-sensitive than many inorganic/alkyl azides but still warrant caution. Avoid grinding and scale-up without risk assessment.
• Incompatibilities: Strong reducing agents (may attack –N3 or nitro group), strong acids/bases (can catalyze rearrangements/decomposition), metals/heavy metal salts (risk of sensitive metal azide formation), and high-intensity UV/heat (promotes nitrene formation/Curtius rearrangement).
• PPE: Safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood; avoid inhalation of dust/aerosols.
• Handling: Minimize dust, avoid mechanical shock, store in original container. For photoreactive azides, protect from intense light/UV.
• First aid (overview): Skin/eye contact—rinse with water for ≥15 min; inhalation—move to fresh air; ingestion—rinse mouth. Seek medical attention in all cases. Defer to SDS for authoritative measures.
• Fire: Use CO2, dry chemical, or foam; cool containers with water spray. Avoid confinement during heating.
• Waste: Quench strategies for organic azides depend on structure; consult institutional guidelines and SDS before disposal.

Solvent Selection

Item-specific solvent data: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for para‑nitro–substituted aryl/acyl azides:

• Polarity/miscibility: Often soluble in moderately polar organics (DCM, EtOAc, THF, MeCN) and in aromatic solvents (toluene). Limited water solubility is common.
• Reaction media selection:
  • Curtius-type rearrangements (for acyl azides): choose inert, anhydrous solvents with good heat transfer (toluene, chlorobenzene, xylene) or polar aprotics (MeCN) when compatible with downstream trapping.
  • Photolysis to nitrenes (aryl azides): use solvents that don’t compete for nitrenes (e.g., non-nucleophilic aliphatics or aromatics). For azide–alkyne cycloadditions, select polar aprotic media (DMF, DMSO, MeCN) to enhance rate; add copper catalyst if using CuAAC.
• Drying/degassing: For moisture-sensitive rearrangements or isocyanate trapping, dry solvents (molecular sieves) and inert atmosphere reduce side reactions.
• Comparison (general):
  • Toluene vs DCM: toluene tolerates higher temperatures for thermal rearrangements; DCM is preferred for low‑temperature photochemistry and easy removal.
  • MeCN vs DMF: MeCN offers lower viscosity and cleaner workups; DMF can accelerate polar reactions but complicates isolation.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (as provided). Protect from direct sunlight and sources of heat. For azide-containing materials, many labs prefer cool, dark storage as a best practice; defer to label/SDS for final instruction.
• Packaging: Not specified for this item; refer to CoA/Spec Sheet. Light-resistant containers are commonly used for aryl azides (general practice).
• Stability: Not specified for this item; refer to CoA/Spec Sheet. Avoid prolonged exposure to UV/visible light and elevated temperatures.
• Reconstitution/stock solutions: If a solid, prepare stocks in dry, oxygen-free organic solvent appropriate to the planned reaction (e.g., MeCN, DCM, DMSO) and store aliquots under inert gas at low temperature if long-term storage is needed (general guidance). Check stability before reuse.
• Freeze–thaw: Not typically applicable unless storing solutions; minimize cycles by aliquoting.
• Research use note: For research use only.

Always consult the lot-specific CoA/SDS for definitive storage, stability, and handling information.

Structure and Identity

• Item name: p-Nitrobenzazide (SKU: P1020345)
• CAS: 17271-88-4; PubChem CID: 11137681
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Provided value “39741” is not a standard InChIKey.)
• 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.

Structural features (general, literature context):

• The name “p‑Nitrobenzazide” is commonly used in the literature for para‑nitro–substituted benzoyl/aryl azide motifs (aromatic ring bearing a para‑NO2 and an azide functionality). Exact structural assignment for this catalog item is not specified here; consult the CoA/SDS for definitive identifiers.
• Aryl azides feature the –N3 group conjugated with an aromatic system; para‑nitro substitution withdraws electron density, influencing photochemistry and Curtius/Schmidt-type reactivity (general literature).
• 2D depiction (general): a benzene ring bearing a para‑nitro group (–NO2) and an azide- or acyl‑azide‑derived functional group; substituent regiochemistry is para relative orientation (general literature).

Synthetic Utility

General synthetic roles for para‑nitro–aryl/acyl azides (verify structural applicability to this item before use):

• Curtius rearrangement platform: Access to para‑nitrophenyl isocyanates, then to carbamates/ureas via trapping with ROH/RNH2. Useful for installing protected amines or generating 4‑nitroaniline derivatives after hydrolysis/reduction.
• Nitrene chemistry: UV or thermal activation enables C–H insertion, ring expansion, or addition to alkenes/arenes. Para‑nitro substituents often stabilize the aryl nitrene and can steer selectivity.
• Triazole synthesis: As the azide component in [3+2] cycloadditions with terminal or internal alkynes, enabling linker formation in materials and bioconjugation contexts.
• Retrosynthetic handle: Converting carboxylic acids to acyl azides (if applicable) provides a pathway to amines via Curtius/hydrolysis, often milder than direct amide reduction.

Operational notes:

• Maintain anhydrous, oxygen- and light-controlled conditions when targeting isocyanates or nitrenes selectively.
• Use dilute conditions and efficient heat removal for rearrangements; vent nitrogen safely.
• Sequence planning: If final targets are anilines, consider incorporating a downstream nitro reduction step (e.g., catalytic hydrogenation or Fe/AcOH) compatible with remaining functionality.

Target Specificity

Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or nucleic acid probe with defined biological target specificity. No item-specific target data are provided.