This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound 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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
395.400 g/mol
XLogP3
3.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Exact Mass
395.092 Da
Monoisotopic Mass
395.092 Da
Topological Polar Surface Area
86.400 Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
614.000
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
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Reseñas
Reseñas de cliente
Application Protocols
No tested application protocols are provided in the Product Data for this item.
General guidance for common research uses (non‑validated; adjust per your assay)
Enzyme inhibition assay (COX activity, in vitro):
Prepare a 10–50 mM DMSO stock. Dilute into assay buffer to desired concentrations, maintaining final DMSO ≤0.5% v/v.
Include vehicle control and a known reference inhibitor for benchmarking.
Measure product formation (e.g., prostaglandin surrogate readout) via ELISA/LC–MS.
Cell‑based assays:
Filter sterilize stock through 0.22 µm PTFE if sterility is required.
Titrate compound to determine cytotoxicity threshold before mechanistic assays.
Analytical reference standard:
Prepare solutions in acetonitrile or methanol for HPLC/LC–MS; verify stability over study duration.
These are provided as general, literature‑style suggestions only. Validate and optimize for your specific system.
Biological Roles
Scope: Research‑only discussion of typical roles for celecoxib‑class diarylpyrazole sulfonamides. No medical or clinical claims.
General roles in chemical biology (literature)
Enzymatic target studies: Widely used as chemical tools to interrogate cyclooxygenase (COX) isoenzymes in vitro (e.g., COX‑1 vs COX‑2 selectivity), enabling SAR elucidation and binding model refinement.
Structural biology: Crystallography and docking benchmarks for understanding binding pocket interactions of arylsulfonamide‑pyrazoles with COX active sites.
Pathway mapping: Employed in vitro to probe prostaglandin biosynthesis steps and feedback regulation in eicosanoid metabolism.
Physicochemical/ADME considerations (general to the class)
Lipophilicity supports membrane permeability in cell‑based assays; limited aqueous solubility often necessitates DMSO stocks and careful vehicle controls.
Sulfonamide H‑bonding can influence target engagement and selectivity.
Assay implementation tips
Use matched controls (inactive analogs or known standards) for specificity assessment in COX activity assays.
Monitor off‑target effects by profiling against related enzymes (e.g., lipoxygenases) in panel screens when mechanistic clarity is required.
Note: The exact potency/selectivity profile of 2‑Methyl‑Celecoxib must be determined experimentally or sourced from peer‑reviewed literature; consult assay data specific to this analog.
Buffer Applications
Not typically applicable. 2‑Methyl‑Celecoxib is a neutral small‑molecule research compound and not used as a buffering agent.
Practical note
When preparing assay solutions, select a biologically relevant buffer (e.g., PBS, HEPES, or Tris) appropriate to the enzyme/cell model, and add the compound from a concentrated DMSO stock to achieve the desired final concentration while keeping DMSO ≤0.1–1% v/v.
Verify compound stability in the chosen buffer over the assay timeframe (e.g., via LC–MS or HPLC).
Green Alternatives
Greener handling of lipophilic diarylpyrazole sulfonamides often focuses on solvent and process choices rather than changing the active scaffold.
2‑MeTHF/EtOAc: Better EHS profiles; may not dissolve highly lipophilic solids as effectively without co‑solvent.
Process considerations
Minimize chlorinated solvents; if used (e.g., DCM for workups), recover via solvent recycling.
Favor room‑temperature operations and catalytic methods in any derivatization workflows.
Evaluate micellar catalysis or aqueous surfactant media for library synthesis when compatible with the scaffold.
Note: Verify solubility and stability of 2‑Methyl‑Celecoxib in any alternative solvent before scale‑up.
Pharmaceutical Uses
This product is supplied strictly for research use only and is not intended for human or veterinary use, drug substance, or excipient applications.
Context for formulation scientists (general, non-clinical)
As a drug‑like research compound, 2‑Methyl‑Celecoxib may be employed as a reference or tool molecule in preformulation studies (e.g., solubility screening, permeability assays) to benchmark methods, but it is not provided to any pharmacopeial monograph or GMP specification.
Typical enabling approaches for poorly water‑soluble arylsulfonamides include co‑solvents (DMSO/ethanol), cyclodextrin inclusion, lipid vehicles, or amorphous dispersions—used only in laboratory research settings.
Regulatory note
No pharmacopeial grade or certification is provided for this item. Any use beyond basic research requires independent qualification and is outside the scope of supply.
Physical Properties
Item-specific properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for celecoxib-class diarylpyrazole sulfonamides (informational; not item specifications)
Physical state: Typically crystalline solids.
Solubility: Commonly sparingly soluble in water; soluble in high‑polarity aprotic organic solvents (DMSO, DMF, NMP) and moderately soluble in chlorinated solvents and alcohols, depending on exact substitution pattern.
Lipophilicity: Generally high (logP > 3 typical for celecoxib analogs; literature class trend).
Ionization: Sulfonamide NH is weakly acidic; pKa often in the 10–11 range for aryl sulfonamides (literature, general).
UV characteristics: Aromatic/azole chromophores absorb in UV; useful for HPLC/UPLC detection (e.g., 210–280 nm). Exact λmax depends on substitution (literature, general).
Do not treat the above as specifications for SKU M991629. For authoritative numeric values (mp, bp, density, refractive index, water or residual solvent levels, UV cutoff), consult the product’s CoA/Spec Sheet and SDS.
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on grades for small‑molecule research compounds
Research grade: Suitable for discovery chemistry, SAR exploration, biological screening, and reference standardization when accompanied by CoA (assay purity by HPLC/UPLC, identity by NMR/HRMS, and residual solvent/moisture).
High‑purity (e.g., ≥98% by HPLC) is often preferred for enzyme assays and biophysical studies to minimize background effects. Verify actual assay % and chromatographic method on the CoA.
Stabilizers: None are typically added for this class; if any stabilizer or salt form is used, it will be disclosed on the label/CoA. Not specified for this item; refer to CoA/Spec Sheet.
Documentation: Expect release tests for identity (1H NMR, MS), purity (HPLC/UPLC with UV), and appearance. Additional tests (water by KF, residual solvents by GC, elemental analysis) may be provided depending on lot.
Practical recommendations
For quantitative work (e.g., analytical reference), confirm assay purity and water content from the specific lot CoA.
If LC–MS quantitation is planned, check UV profile and potential late‑eluting impurities; consider orthogonal purity checks (qNMR) when critical.
Reaction and Applications
Research applications (non-clinical)
Chemical probe: 2‑Methyl‑Celecoxib, as a celecoxib‑class analog, is commonly used to study cyclooxygenase (COX) isoform selectivity, structure–activity relationships (SAR), and binding thermodynamics in enzymology and chemical biology (literature, general for the class).
Reference standard: Useful as a comparator or internal standard in analytical methods during medicinal chemistry campaigns targeting COX‑related pathways.
Derivatization opportunities (synthetic context)
Sulfonamide functional handle: May be derivatized (e.g., N‑acylation, N‑sulfonylation, carbamate formation) to generate analog libraries or pro‑moieties for target engagement studies.
Pyrazole ring: N‑alkylation or electrophilic substitution (where permitted by substitution pattern) can modulate physicochemical properties; protect/deprotect strategies may be employed.
Aromatic rings: Electrophilic aromatic substitution on appropriately activated positions can enable late‑stage diversification; however, substitution patterns in celecoxib analogs often limit available positions.
Analytical applications
LC–UV/LC–MS method development using UV‑active aromatic/azole chromophores; typical detection at 210–280 nm.
Stability studies in buffer and microsomal matrices (literature practice) to understand metabolic liabilities of the scaffold.
Practical tips
Stock preparation: Dissolve in dry DMSO; filter (0.22 µm PTFE) for bioassay stocks when sterility/particulate control is required.
Light/moisture: No special sensitivity is typical, but store tightly closed and avoid prolonged heating to prevent degradation.
Reaction Conditions
This section provides general, literature‑based conditions relevant to derivatizing celecoxib‑class diarylpyrazole sulfonamides. These are not specifications for this item.
Typical conditions (examples)
Sulfonamide N‑acylation: Acid chloride or anhydride (1.1–1.5 equiv), base (Et3N, DIPEA, or pyridine), solvent (DCM, THF, or MeCN), 0–25 °C, 1–4 h; workup with aqueous bicarbonate.
Sulfonamide N‑alkylation: Alkyl halide (1.2–2.0 equiv), base (K2CO3, Cs2CO3, or NaH), solvent (DMF/MeCN), 20–60 °C, 2–16 h; monitor by TLC/LC–MS.
Pyrazole N‑alkylation: NaH (1.1–1.5 equiv) in THF/DMF at 0–25 °C, then add alkyl bromide/iodide; quench carefully; purify by column chromatography.
Electrophilic aromatic substitution (where available): Nitration (AcOH/HNO3, 0–5 °C), halogenation (NBS/NCS, solvent‑controlled). Regiochemistry must be verified experimentally.
Analytical monitoring
HPLC or UPLC (C18, water/MeCN + 0.1% formic acid) with UV at 230–254 nm; LC–MS (ESI+) typically provides good ionization for sulfonamides.
Yields
Typical isolated yields for these modifications range from moderate to good (40–85%), depending on substitution and sterics (literature, general).
Caveats
Competing deprotonation of the sulfonamide vs pyrazole can occur; choose base/solvent to favor the intended site.
Avoid strong prolonged heating to limit desulfonylation or decomposition.
Safety and Handling
Item-specific hazard data
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General safety guidance for diarylpyrazole sulfonamides (informational; defer to SDS)
Expected hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Avoid dust generation.
PPE: Laboratory coat, safety glasses or face shield, and suitable gloves (e.g., nitrile). Handle in a fume hood to minimize inhalation of particulates.
First aid (overview):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: Rinse with plenty of water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: Rinse mouth; seek medical attention.
Handling: Avoid dust/airborne particulates. Use anti-static measures when weighing fine powders. Keep containers tightly closed.
Incompatibilities: Strong oxidizers, strong bases/acids may react with sulfonamides/azole rings; avoid reactive acylating agents unless used intentionally in derivatization.
Fire safety: Organic solids are combustible. Use CO2, dry chemical, or foam; avoid high‑pressure water streams that may disperse powders.
Waste: Dispose according to institutional and local regulations for organic laboratory chemicals.
Always consult the product SDS for definitive hazard classification, exposure limits, and spill/fire response.
Solvent Selection
Applicability: This section focuses on dissolving a lipophilic diarylpyrazole sulfonamide for analytical solutions, stock prep, and biotesting.
General solvent behavior (literature, class-based)
Preferred solvents for stock solutions: DMSO (most common), DMF, NMP. These offer high solvating power for aromatic heterocycles and sulfonamides.
Secondary options: Acetonitrile, methanol, ethanol, isopropanol, dichloromethane, ethyl acetate. Solubility may be moderate and can benefit from mild warming or sonication.
Aqueous media: Poor intrinsic water solubility is typical. For biological assays, prepare concentrated DMSO stocks (e.g., 10–50 mM), then dilute into buffered media keeping final DMSO ≤0.1–1% v/v as assay‑compatible.
Polarity and detection considerations
Polarity: Overall nonpolar to moderately polar, dominated by aromatic rings; sulfonamide contributes H‑bonding capacity.
Chromatography: Reverse‑phase (C18, phenyl‑hexyl) with water/acetonitrile or water/methanol and 0.1% acid (formic or TFA) typically gives robust peak shape.
Small comparison (general)
DMSO: Highest solubility; viscous; excellent for bio stocks.
DMF/NMP: Similar solvating ability; consider toxicity/handling.
MeOH/EtOH: Greener, but limited solubility; may suffice for analytical standards at lower concentrations.
Always confirm actual solubility and stability for this specific item with a small trial or CoA notes when available.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (as provided in Product Data). Store in original, tightly closed container, protected from excessive heat and moisture.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General reconstitution guidance (informational; not item specifications)
Stock solutions: Dissolve the solid in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Record exact concentration gravimetrically.
Working solutions: Dilute stock into assay buffer or culture medium immediately before use, keeping the final DMSO fraction within assay‑tolerated limits (commonly ≤0.1–1% v/v).
Filtration: If particulate control or sterility is required, pass solutions through a 0.22 µm PTFE syringe filter.
Stability: Avoid repeated freeze–thaw of DMSO stocks; aliquot into single‑use vials. Store aliquots at −20 °C for extended periods if needed (general practice) and protect from light.
Labeling and documentation
Record lot number, preparation date, solvent, and concentration on all stock vials.
For definitive stability, re-test intervals, and any special precautions, consult the lot-specific CoA and SDS.
Structure and Identity
Brief description: 2‑Methyl‑Celecoxib is a diarylpyrazole sulfonamide analog of celecoxib, typically used as a small‑molecule research probe in COX‑related enzymology and medicinal chemistry.
Item-specific (from Product Data)
SKU: M991629
Product name: 2-Methyl-Celecoxib
CAS: 170570-09-9
InChIKey: 41339 (as provided)
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 features (for celecoxib-class diarylpyrazole sulfonamides)
Core scaffold: 1,3,5‑substituted pyrazole with two aryl rings (diarylpyrazole) and a sulfonamide (–SO2NH2) on one aryl ring.
Typical substituents: One aryl ring often bears a sulfonamide; the other frequently carries a lipophilic group such as –CF3 and aryl alkyl substituents. The “2‑methyl” descriptor commonly denotes an ortho‑methyl on one phenyl ring (literature, class description), but confirm exact regiochemistry from the CoA/Spec Sheet.
Functional groups: Aromatic rings, pyrazole (azole heterocycle), sulfonamide, and often a trifluoromethyl (class motif).
2D description in words (general for the class)
A central pyrazole ring substituted at N1 with a para‑sulfonamidophenyl and at C3/C5 with an aryl ring and an electron‑withdrawing/lipophilic group; “2‑methyl” indicates an additional methyl substituent on one aryl ring. Verify precise connectivity with the item’s CoA.
Synthetic Utility
Although 2‑Methyl‑Celecoxib is itself a final analog, it can serve as a platform for further derivatization and as a reference scaffold in synthesis and SAR.
Transformations and handles (general to the class)
Sulfonamide derivatization: N‑acylation, N‑alkylation (with appropriate base and alkyl electrophiles), or formation of urea/carbamate motifs to tune physicochemical properties.
Pyrazole N‑functionalization: Under basic conditions (e.g., NaH, K2CO3), N‑alkylation can modulate lipophilicity and metabolic stability if the N‑position is unsubstituted/accessible.
Aromatic modifications: Electrophilic aromatic substitution (nitration, halogenation, sulfonylation) may be feasible at unblocked positions for late‑stage diversification; regiochemistry governed by existing substituents.
Retrosynthetic context (celecoxib-class)
Commonly assembled via condensation of hydrazines with 1,3‑dicarbonyl equivalents to form the pyrazole, followed by arylation and sulfonamide installation. Trifluoromethyl introduction often uses CF3‑bearing building blocks or electrophiles.
Analytical and purification
Reverse‑phase chromatography (C18) and normal‑phase silica with gradient EtOAc/hexanes or DCM/MeOH systems are effective. Monitor by UV (210–280 nm) and LC–MS.
Note: Actual reactive sites of this specific analog depend on its exact substitution pattern; consult structural data in the CoA.
Target Specificity
Not applicable to this catalog item. This product is a small‑molecule compound, not an antibody or affinity reagent.
Context (general)
Celecoxib‑class analogs are commonly investigated as selective binders to COX isoenzymes in biochemical assays. However, no target specificity, potency, or selectivity data are provided for this specific item in the Product Data. Consult the primary literature or generate in‑house assay data for definitive profiling.
Preguntas frecuentes
What is the purity of this product?
This product is supplied at ≥95% 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 170570-09-9, the molecular formula is C18H16F3N3O2S, and the molecular weight is 395.4 g/mol. InChIKey CDMHSMOZNZFYIK-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.
Utilizamos cookies para garantizar el correcto funcionamiento del sitio web y, cuando esté permitido, para mejorar su experiencia. Puede gestionar sus preferencias en cualquier momento en Configuración. Más información en nuestra Política de Cookies.
¿Quieres que te enviemos un mensaje cuando tengamos descuentos disponibles?
Recordármelo más tarde
¡Gracias! Por favor, revisa tu bandeja de entrada de correo electrónico para confirmar.
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.
