N-Phenylsydnone - ≥97% , CAS No.120-06-9

CAS: 120-06-9 Cat. No.: N1071721 Summenformel: C₈H₆N₂O₂ Molekulargewicht: 162.15 EG-Nummer: 815-129-5 PubChem CID: 123023

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Reinheit

≥97%

Namen und Kennungen

Kanonisches Lächeln

C1=CC=C(C=C1)[N+]2=NOC(=C2)[O-]

IUPAC Name

3-phenyloxadiazol-3-ium-5-olate

InChIKey

KQEVEDHJIGSXDK-UHFFFAOYSA-N

INCHI

1S/C8H6N2O2/c11-8-6-10(9-12-8)7-4-2-1-3-5-7/h1-6H

Isomere SMILES

C1=CC=C(C=C1)[N+]2=NOC(=C2)[O-]

PubChem CID

123023

Molekulargewicht

162.15

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Heteroaromatic compounds 1,2,3-oxadiazoles Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Monocyclic benzene moiety - Azole - Oxadiazole - 1,2,3-oxadiazole - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic zwitterion - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 162.150 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.043 Da
• Monoisotopic Mass: 162.043 Da
• Topological Polar Surface Area: 53.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 148.000
• 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

No tested bioassay or immunoassay application protocols are provided for this small‑molecule product. For synthetic use, refer to the Reaction Conditions and Application notes in this page. For bioconjugation via strain‑promoted sydnone–alkyne cycloaddition, optimize concentration (0.1–2 mM), buffer (near neutral pH), and stoichiometry (1.2–2.0 equiv alkyne) empirically for your system (literature guidance).

Biological Roles

• Product Data (item-specific)

  • Research Use Note: For research use only

• Literature/General (non-item-specific)

  • N‑Phenylsydnone is a synthetic mesoionic small molecule without a native biological role. Its chief relevance to biology is methodological: as a 1,3‑dipole precursor for bioorthogonal conjugation using strain‑promoted sydnone–alkyne cycloaddition (SAC), enabling labeling of biomolecules modified with strained alkynes (e.g., DBCO/BCN conjugates).
  • In enzymology or metabolism studies, sydnones can serve as chemical probes or precursors to pyrazole motifs, but they are not endogenous metabolites.
  • Any discussion of pharmacology is outside scope here; this product is intended strictly for laboratory research applications.

Buffer Applications

N‑Phenylsydnone is not a buffer component and does not serve as an acid/base buffering agent. For bioorthogonal conjugations (literature), sydnone–alkyne cycloadditions can be performed in common buffers (e.g., PBS, HEPES) with organic cosolvent (5–20%) to aid solubility of hydrophobic partners. Optimize pH near neutrality to limit base‑induced decomposition.

Green Alternatives

• Greener processing choices for sydnone chemistry (literature; general guidance)

  • Solvent selection: prioritize EtOAc or MeCN over chlorinated solvents; for high‑temp runs, consider anisole or propylene carbonate as higher‑boiling, lower‑toxicity options. For SAC, aqueous/biocompatible media (buffer/MeOH/H2O) are effective.
  • Energy: microwave or flow chemistry can reduce thermal budgets and improve safety for scale‑up.
  • Workup: use aqueous micellar extractions or solvent‑minimized crystallizations to curtail VOC use.

• Comparison (illustrative; non‑item‑specific)

  • Conventional: toluene/xylene at 120–140 °C for 6–16 h; chlorinated solvents for handling.
  • Greener alternative: ethanol, EtOAc, or MeCN at lower temperatures with catalysts or with strained alkynes at rt in aqueous buffer; reduced solvent hazard and energy use.

• Trade‑offs

  • Polar green solvents can complicate isolation (salting‑out or antisolvent crystallization may be needed).
  • Strained alkynes are costlier but enable room‑temperature, metal‑free conditions and water compatibility.

Pharmaceutical Uses

• Item-specific: No pharmacopeial status, excipient role, or GMP suitability is specified for this product; refer to CoA/Spec Sheet.

• Literature/General (non-therapeutic context)

  • N‑Phenylsydnone is used in discovery and process chemistry as a precursor to N‑phenyl‑substituted pyrazoles, a motif frequently encountered in agrochemical and pharmaceutical candidates.
  • In conjugation/process steps, its clean CO2 extrusion can reduce by‑product burdens, aiding downstream purification. Any application in regulated manufacturing would require independent qualification and specifications not provided here.

Physical Properties

• Product Data (item-specific)

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

• Literature/General (non-item-specific; typical values reported for N‑phenylsydnone)

  • Phase at ambient conditions: crystalline solid (literature)
  • Solubility profile: generally soluble in chlorinated solvents (e.g., CH2Cl2), ethyl acetate, acetonitrile, THF, DMF/DMSO; sparingly soluble in hexanes; low aqueous solubility (literature, qualitative).
  • Polarity/behavior: mesoionic heterocycle with significant dipolar character; behaves as a 1,3‑dipole precursor in cycloadditions (literature).

• Not specified for this item; refer to CoA/Spec Sheet for any of the following if needed in a regulated workflow:

  • Melting point, boiling point, density, refractive index, logP, pKa, UV cutoff, metal/peroxide/water limits.

Quality and Grades

• Product Data (item-specific)

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

• Interpreting grades (general guidance)

  • Research grade: intended for laboratory R&D. Unless otherwise specified, not certified for GMP processes.
  • Chromatography/HPLC grades (if applicable in other listings) emphasize low nonvolatile residue and low UV absorbance; not implied here without explicit specification.
  • Metal content, water content (KF), and residual solvent profiles are important for cycloaddition workflows and catalytic studies but are not specified for this item; refer to the CoA for lot‑specific data if required.

• Stabilizers/additives

  • No stabilizer is listed for this item. If ultra‑dry or inhibitor‑free material is required for sensitive reactions, verify via CoA or pre‑dry in vacuo at ambient temperature to constant mass.

• Recommended incoming QC (user practice)

  • Confirm identity by 1H/13C NMR and HRMS; sydnones show characteristic downfield signals and IR C=O‑like stretch near 1750–1800 cm−1 (literature). Assess residual solvents by GC/HS‑GC if critical.
  • If using in click‑type cycloadditions, a small test reaction with a standard alkyne (e.g., phenylacetylene or BCN) can validate reactivity profile.

Reaction and Applications

• 1,3‑Dipolar cycloadditions to alkynes (literature)

  • N‑Phenylsydnone acts as an azomethine imine 1,3‑dipole donor, undergoing cycloaddition with terminal, internal, or strained alkynes to furnish N‑phenyl‑substituted pyrazoles, typically with extrusion of CO2. Regiochemistry depends on alkyne substitution and electronics.
  • Strain‑promoted sydnone–alkyne cycloaddition (SAC) with cyclooctynes (e.g., BCN, DBCO) proceeds rapidly at ambient temperature and is used as a metal‑free “click‑like” transformation.

• Heterocycle synthesis (literature)

  • Access to 1,3,4‑ and 1,3,5‑substituted pyrazoles after downstream manipulations. N‑Phenyl substituent on the pyrazole nitrogen is introduced intrinsically from the sydnone.

• Materials/labeling (literature)

  • Sydnone–alkyne conjugation strategies are applied to surface modification and polymer functionalization, where CO2 extrusion provides high driving force and benign by‑product.

• Practical tips

  • Purity matters: residual amines or strong bases can diminish yields via decomposition. Use neutral to mildly acidic conditions when feasible.
  • Microwave assistance can shorten reaction times substantially for unactivated alkynes.
  • For terminal alkynes, copper(I) salts or Lewis acids may enhance rates/selectivity in some systems; evaluate on small scale first.
  • Monitor by LC–MS: disappearance of sydnone mass and appearance of pyrazole + 44 mass deficit (CO2 loss) is diagnostic.

Reaction Conditions

• General guidance for sydnone–alkyne cycloadditions (literature; non-item-specific)

  • Thermal (unactivated alkynes): 0.5–1.5 equiv sydnone, 1.0–1.5 equiv alkyne; toluene/xylene or chlorobenzene; 100–140 °C; 2–16 h; typical isolated yields 50–90% depending on alkyne electronics.
  • Polar aprotic media: DMF/DMSO/MeCN can accelerate reactions at 60–100 °C; facilitate microwave heating (10–60 min total time) with similar or improved yields.
  • Strain‑promoted (BCN/DBCO): room temperature in MeCN/H2O, DMSO/H2O, or buffered aqueous media (pH ~7–8) with 5–20% organic cosolvent; 0.1–2 mM typical for bioconjugations; reaction half‑times minutes to hours; near‑quantitative conversions common with slight excess of cycloalkyne.
  • Catalysis: Cu(I), Ag(I), or Lewis acids have been reported to enhance rates/regioselectivity for certain terminal/internal alkynes; catalytic loadings 1–10 mol% at 25–80 °C.

• Monitoring and workup

  • Monitor by TLC (UV) or LC–MS; CO2 evolution is not directly visible in solution but correlates with product formation. Quench, extract with EtOAc, wash brine, dry (Na2SO4), and purify by silica gel. Pyrazoles often elute with moderately polar eluents (e.g., hexanes/EtOAc 2:1 to 1:2).

• Safety notes

  • Avoid sealed‑tube overheating without venting; CO2 evolution increases internal pressure. Conduct small‑scale pressure testing before scale‑up. Ensure adequate stirring to prevent hot spots.

Safety and Handling

• Product Data (item-specific)

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H‑Statements / P‑Statements / Pictograms: Not specified for this item; refer to SDS.

• General hazards and precautions for sydnones (literature/experience; defer to SDS for authoritative data)

  • Although many sydnones are handled routinely as bench‑stable solids, they are energy‑rich mesoionic compounds; avoid grinding, friction, or rapid heating of large quantities. Scale up cautiously and conduct thermal screening if needed.
  • Avoid contact with strong bases (can induce decomposition), strong reducing agents, and strong oxidizers. Thermal decomposition may release CO2 and nitrogenous gases.
  • Engineering controls: use in a fume hood to avoid dust inhalation and solvent vapors during reactions.
  • PPE: lab coat, safety glasses, nitrile gloves; use a dust mask or respirator if generating particulate.
  • First aid (overview; consult SDS): rinse eyes/skin with water for ≥15 min upon contact; move to fresh air if inhaled; seek medical attention if symptoms persist. If ingested, rinse mouth—do not induce vomiting unless directed by medical personnel.
  • Fire response: treat as an organic combustible; use CO2, dry chemical, or foam. Cool containers with water spray from a safe distance.

• Stability/handling tips

  • Store at room temperature in a tightly closed container, away from heat sources and direct sunlight. Keep dry and segregated from strong bases/oxidants.
  • For reactions, add to preheated media carefully and avoid hot‑spot formation.

Solvent Selection

N‑Phenylsydnone is a neutral but highly polarized mesoionic solid; solvent choice impacts both stability and 1,3‑dipolar cycloaddition rates.

• General miscibility/solubility (literature)

  • Good: CH2Cl2, CHCl3, EtOAc, MeCN, THF, dioxane, DMF, DMSO.
  • Moderate: toluene, xylene (often used for high‑temp cycloadditions).
  • Poor: aliphatic hydrocarbons (hexanes/heptane). Low water solubility.

• Selection guidance by task

  • Routine handling/transfer: CH2Cl2 or EtOAc give rapid dissolution and convenient removal.
  • Thermal cycloadditions: toluene, xylene, or chlorobenzene allow 90–140 °C operation; polar aprotic solvents (DMF/DMSO) can accelerate but complicate workup.
  • Strain‑promoted cycloadditions (SAC) and bioconjugation: aqueous cosolvent systems (e.g., MeCN/H2O, DMSO/H2O, or buffered media with ≤10–20% organic) improve compatibility; choose solvent system based on alkyne partner solubility.

• Comparison notes (literature)

  • Polar aprotic solvents often increase rate for sydnone–alkyne cycloadditions, but aromatic solvents can favor cleaner profiles at high temperature.
  • For moisture‑sensitive downstream steps, choose dry MeCN/THF and perform gentle vacuum drying after reaction.

Storage and Reconstitution

• Product Data (item-specific)

  • Storage Conditions: Room temperature

• General storage guidance

  • Store tightly sealed, in a dry place, away from direct light and heat sources. Desiccation helps maintain consistency for analytical weighing and mitigates hydrolytic/background decomposition over long periods.
  • Keep segregated from strong bases, oxidizers, and reducing agents. Avoid prolonged exposure to high temperatures.

• Reconstitution/solution handling

  • Prepare stock solutions in dry CH2Cl2, MeCN, THF, or DMSO as needed for immediate use. For longer storage, prefer amber vials under inert gas at 2–8 °C to minimize slow degradation (literature precaution); verify stability by LC–MS/NMR before critical experiments.
  • Avoid highly basic media during storage; neutral to slightly acidic conditions are preferred for solution stability.

• Shipping

  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Shelf life

  • Not specified for this item; refer to CoA/Spec Sheet. As a best practice, re‑assay material periodically if stored in solution.

Structure and Identity

Concise mesoionic heteroaromatic used as a 1,3‑dipole precursor for pyrazole synthesis.

• Product Data (item-specific)

  • CAS: 120-06-9
  • SKU: N1071721
  • Storage Conditions: Room temperature
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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 structural description (non-item-specific)

  • Common name: N‑Phenylsydnone (a mesoionic 1,2,3‑oxadiazol‑3‑ium‑5‑olate with an N‑phenyl substituent)
  • Core features: 5‑membered sydnone ring (1,2,3‑oxadiazole valence isomer) bearing an exocyclic carbonyl character and internal charge separation; N‑aryl substitution (phenyl) on the ring nitrenium center.
  • Functional groups: mesoionic azomethine imine, N‑aryl substituent, and a carboxylate‑like moiety embedded in the ring; overall neutral but highly polarized.
  • 2D description in words: A phenyl ring is bonded to the endocyclic nitrogen of a 5‑membered ring containing two adjacent nitrogens and one oxygen; the ring exhibits a zwitterionic resonance with a carbonyl/olate character opposite the N‑phenyl bond.

Synthetic Utility

• Functional reactivity (literature)

  • Acts as a mesoionic azomethine imine equivalent; undergoes [3+2] cycloadditions with alkynes to yield pyrazoles after CO2 extrusion. Electronic/steric tuning of the alkyne directs regiocontrol.
  • Compatible with a range of alkynes: terminal, internal, heteroatom‑substituted, and strained cycloalkynes. Aromatic alkynes often react faster than aliphatic ones.

• Retrosynthetic value

  • Provides direct access to N‑phenyl‑substituted pyrazoles without N‑arylation steps, simplifying routes when the N‑phenyl group is desired.
  • Late‑stage diversification: conjugation onto complex alkynes (small molecules, polymers, surfaces, or biomolecule handles) under mild conditions.

• Orthogonality and downstream chemistry

  • The resulting pyrazoles tolerate hydrogenation, cross‑coupling (if handles present), and electrophilic substitution. Protective groups generally unnecessary during SAC due to metal‑free, neutral conditions.

• Practical considerations

  • Moisture/base sensitivity is modest but real; maintain neutral conditions for storage/handling. For challenging substrates, use microwave heating or catalytic activation to improve conversions.

Target Specificity

Not applicable. This product is a small‑molecule heterocycle, not an antibody, enzyme, or ligand with defined biological target specificity. No item‑specific target data are provided.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 120-06-9, the molecular formula is C8H6N2O2, and the molecular weight is 162.15 g/mol. InChIKey KQEVEDHJIGSXDK-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.