This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
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
345.130 g/mol
XLogP3
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Exact Mass
343.997 Da
Monoisotopic Mass
343.997 Da
Topological Polar Surface Area
96.200 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
404.000
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
2
Calculadoras de soluciones
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Application Protocols
No application protocols are specified for SKU N768896.
General laboratory practices (research use)
Stock preparation: Dissolve in dry DMSO to 10–50 mM; vortex and sonicate if needed. Filter (0.22 µm PTFE) for particulate removal if required for analytical work.
Dilution: Add DMSO stock to assay buffer or media with thorough mixing to avoid local supersaturation; keep final DMSO content within assay tolerance.
Solid handling: Minimize moisture exposure to maintain defined hydrate content; record mass promptly and cap containers immediately.
For assay‑specific protocols (e.g., cell‑based screens, analytical calibrations), refer to your internal SOPs or primary literature.
Biological Roles
Context for research only (no clinical or therapeutic claims)
Chemical class: Chlorinated salicylanilide with a nitro substituent; weak acid with high lipophilicity.
Biochemical behavior (literature): Compounds in this class often act as protonophores/uncouplers at membranes and can impact cellular energy metabolism in model systems. Specific interactions include potential binding to proteins via hydrogen bonding and π–π contacts, and pH‑dependent ionization that affects membrane partitioning.
Ionization and partitioning: At physiological pH, the neutral form predominates (given phenolic pKa ~6.5–7.5), favoring membrane association; in basic environments, the phenolate is more water‑soluble and less membrane‑permeant.
Assay considerations: The nitroaromatic chromophore yields strong UV absorbance that is useful for spectrophotometric quantification; fluorescence can be quenched by nitro groups. Protein binding may be significant due to hydrophobicity and aromaticity.
Metabolism and transformations (literature, in vitro): Potential phase II conjugation (e.g., glucuronidation/sulfation of the phenolic OH) and nitro reduction in certain reductive environments. These routes inform metabolite identification workflows and analytical method development.
Use in the lab
Employed as a reference compound in transporter/efflux, mitochondrial function, and permeability assays in cell‑free or cell‑based models under controlled conditions.
Note: These are general research observations for the chemical class; consult primary literature for system‑specific behavior. No biological performance is implied for SKU N768896.
Buffer Applications
Not typically used as a buffering agent.
Practical notes for working in aqueous buffers (research use)
Aqueous dissolution: Poorly soluble at neutral pH. To prepare buffered solutions, first dissolve in DMSO to make a concentrated stock, then dilute into buffer (keep final DMSO ≤0.1–1% v/v as compatible with the assay).
pH‑assisted solubilization: Dissolution can be enhanced by adjusting buffer to pH ≥8–9 to form the phenolate; confirm that basic conditions are acceptable for your experimental system and that re‑protonation will not precipitate the compound during downstream steps.
Surfactants/cyclodextrins: For specialized studies, nonionic surfactants or cyclodextrins may improve apparent solubility (screen empirically).
For buffering needs, use dedicated buffer systems (e.g., phosphate, Tris, HEPES) rather than this compound.
Green Alternatives
As a solid active compound rather than a bulk solvent, “green alternatives” primarily concern solvent and process choices for dissolving, formulating, or derivatizing niclosamide monohydrate.
Greener handling strategies (literature-informed)
Prefer greener solvents where feasible: ethanol and isopropanol for recrystallization or low‑concentration solutions; ethyl acetate or 2‑MeTHF for extractions/workups instead of chlorinated solvents.
Aqueous basic dissolution: Temporarily convert to the phenolate in carbonate/bicarbonate buffer to avoid high‑boiling dipolar aprotic solvents; re‑acidify as needed.
Process intensification: Use minimal DMSO volumes and high‑throughput vial formats to limit solvent waste in screening.
Mechanochemistry: For derivatization or cocrystal formation, consider ball milling with catalytic base to reduce solvent use (where compatible).
Small comparison (typical choices)
DMSO vs ethanol
Solubility: DMSO >> ethanol
Greenness/tox profile: ethanol preferable
Impact: DMSO can affect bioassays at low %; ethanol tolerance often higher but achievable concentrations lower
DMF/NMP vs 2‑MeTHF/EtOAc
Reactivity media: DMF/NMP superior for O‑alkylation; greener alternatives acceptable for extractions and some recrystallizations
Tradeoffs
Greener solvents may not reach the concentrations needed for high‑throughput stocks. Consider two‑step workflows (concentrated DMSO master + greener diluent) to balance performance and sustainability.
Pharmaceutical Uses
For research and laboratory use only.
Relevant non-clinical, preformulation, and QC contexts (no therapeutic claims)
Reference standard: Used as a system suitability or identity/assay standard in analytical methods for salicylanilides. Ensure the hydrate form matches the method’s mass balance (account for 1 mol H2O per mol analyte).
Solid‑state form work: Monohydrate enables studies of hydrate stability, polymorph screening, and dehydration/rehydration kinetics (TGA/DSC/PXRD), informing formulation strategies in preformulation research.
Solubility/permeability studies: Supports BCS‑style investigations and salt/cocrystal screening to modulate solubility for research.
Excipient compatibility screens: Evaluate interactions with common excipients (e.g., microcrystalline cellulose, lactose, PVP) under ICH conditions to understand stability pathways (e.g., base‑catalyzed hydrolysis, nitro reduction risk with reducing excipients).
Impurity profiling: Nitroaromatic and salicylanilide‑related degradants can be profiled via LC–MS; hydrate water content may influence degradation rates.
Regulatory note
No pharmacopeial grade or monograph status is stated for SKU N768896. If compendial compliance is required for your lab work, verify against the relevant pharmacopoeia and obtain a CoA demonstrating conformance.
Physical Properties
Item-specific specs for this catalog entry
Appearance: 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/reference properties for niclosamide monohydrate (for planning; not item specifications)
Physical state: crystalline solid (literature for niclosamide forms).
Melting behavior: anhydrous niclosamide reported mp ~230–236 °C; monohydrate may show dehydration endotherm followed by melt/decomposition above ~200–230 °C (literature; varies with polymorph and water content).
Solubility (25 °C, literature):
Water: very low (reported <1 mg/L; pH-dependent due to phenolic acidity).
Organic: soluble in polar aprotic solvents (DMSO, DMF, NMP); sparingly to moderately soluble in acetone/ethyl acetate; low solubility in nonpolar hydrocarbons.
pKa (literature): phenolic OH pKa ~6.5–7.5; amide is nonbasic; deprotonation markedly increases aqueous solubility at basic pH.
UV–Vis (literature): strong π–π* absorbance in near‑UV; nitro-substituent confers charge‑transfer bands; exact λmax depends on solvent/ionization state.
Hygroscopicity: exists as monohydrate; may gain/lose water depending on humidity and temperature (literature observation for hydrates).
Notes
Always confirm form (hydrate vs anhydrate) and polymorph by PXRD/TGA/DSC if properties are critical.
Values above are typical literature ranges and are not specifications for SKU N768896.
Quality and Grades
Grade/purity for this catalog item: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grade for niclosamide monohydrate (general guidance)
When grade is declared (e.g., ≥98%, ≥99%): This reflects assay of the specified hydrate form, typically by HPLC/LC–MS and/or qNMR, and may include water content by KF to confirm monohydrate stoichiometry. For hydrates, purity often refers to the organic component, while water of crystallization is quantified separately.
UV/LC suitability: If an HPLC/analytical grade is indicated, expect tighter control of nonvolatile residues and low-level aromatic impurities that can interfere with chromatographic or spectroscopic analyses.
Residual solvents/metals: Unless explicitly stated on the CoA, these are not guaranteed. Request CoA for specific residual profiles if your application is impurity-sensitive (e.g., reference standards, method development).
Form verification: Hydrate vs anhydrate can influence mass balance and dissolution. For quantitative work, confirm water content (Karl Fischer) and, if necessary, dry under controlled conditions to the desired form.
What is specific to SKU N768896
Storage: 2–8 °C; shipped on wet ice (helps preserve solid form and hydration state during transit).
For research use only (per Product Data). No clinical or in vivo use is implied.
Recommendation
Obtain and review the CoA/Specification Sheet for batch-specific assay, water content, residual solvents, and any declared stabilizers or form descriptors (e.g., polymorph, particle size).
Reaction and Applications
This product is typically used as a reference compound or research tool rather than a reagent; however, its functional groups enable diverse transformations and formulation strategies.
Research uses (general)
Analytical standard: Employed in method development/validation (HPLC/LC–MS) for salicylanilide quantification, stability studies, and dissolution testing (literature practice). Ensure use of the correct hydrate for mass balance.
Probe compound: Utilized in chemical biology and screening to interrogate pathways sensitive to salicylanilide scaffolds; stock preparation considerations dominate (see Solvent Selection).
Transformations and derivatization (synthetic chemistry, literature)
O‑alkylation/acylation: Phenolic OH can be protected or diversified to modulate solubility and permeability.
N‑acyl or N‑arylation is not applicable to the amide nitrogen (already acylated), but the amide can undergo coupling chemistry for conjugates (e.g., carbonyldiimidazole activation of the phenol followed by nucleophiles).
Nitro group chemistry: Chemoselective reduction to anilines (e.g., catalytic hydrogenation, Fe/AcOH, SnCl2) affords derivatives for SAR.
Halogen substituents: Enable cross‑coupling (e.g., Suzuki, Buchwald–Hartwig after nitro reduction) to access analog libraries.
Practical tips
Maintain control of hydration: Confirm water content by KF before stoichiometric reactions or quantitative standards.
Solubilization: Use DMSO or phase‑transfer conditions for O‑alkylations; bases such as K2CO3/Cs2CO3 in DMF/acetone are common.
Stability: Avoid strong bases for prolonged periods to limit amide hydrolysis or undesired O/N‑acyl migration.
Note: No manufacturer‑specific application notes were provided for this SKU; the above summarizes common literature practices.
Reaction Conditions
General literature guidance for typical transformations on niclosamide‑like scaffolds (for planning; adapt to your system)
O‑Alkylation of phenol
Solvent: DMF, DMSO, or acetone.
Base: K2CO3 or Cs2CO3 (1.5–2.0 eq).
Electrophile: Alkyl halide (1.2–1.5 eq).
Temperature/time: 25–60 °C, 2–16 h.
Notes: Compete with N‑alkylation is minimal due to amide; water reduces rate.
Nitro reduction to aniline
Catalyst: 5–10% Pd/C (5–20 wt% to substrate) under H2 (1–3 bar).
Solvent: EtOH, EtOAc, or THF; add base (e.g., NaHCO3) to buffer acidity.
Temperature/time: RT to 50 °C, 1–6 h.
Alternative: Fe/AcOH or SnCl2/EtOH for chemoselective reductions.
Suzuki–Miyaura coupling (on aryl chloride site)
Catalyst/base: Pd(PPh3)4 (2–5 mol%) or Pd2(dba)3/XPhos with K3PO4 or Cs2CO3.
Solvent: 1,4‑dioxane/H2O or toluene/H2O; 80–110 °C.
Time: 6–18 h.
Notes: Nitro group can be tolerated; phenolic protection may improve yields.
Protective group strategies
Phenol protection: TBDMS‑Cl/imidazole (DMF) or benzylation (BnBr/K2CO3) to prevent O‑metalation during coupling; deprotect by TBAF (for silyl) or hydrogenolysis (for Bn).
Analytical/processing
Quantitation: UV at near‑UV wavelengths; LC–MS with ESI(−) often suitable due to phenolate formation.
Workup: Given low water solubility (neutral form), aqueous workups often afford high recoveries; basic washes increase partitioning to aqueous phase (plan accordingly).
All parameters are literature‑style starting points; perform small‑scale optimization for your substrate and equipment.
Safety and Handling
GHS/label information for this item
Signal word, H‑statements, pictograms, and classification: Not specified for this item; refer to the product SDS for authoritative information.
General safety guidance (literature-informed; not a substitute for SDS)
Hazards: Aromatic nitro/salicylanilide compounds can present acute toxicity and are harmful if swallowed or inhaled; dust may cause respiratory and eye irritation. Avoid environmental release.
PPE: Wear lab coat, suitable gloves (e.g., nitrile), safety glasses or face shield. Use in a fume hood to minimize dust exposure.
Handling: Avoid generating dust/aerosols. Use dedicated tools and weigh boats. Wash thoroughly after handling. Prevent release to drains.
Storage: Store at 2–8 °C (per Product Data), tightly closed in the original container. Protect from excessive heat, direct light, and high humidity to preserve hydration state.
Incompatibilities (general): Strong oxidizers and strong bases/acids can alter the compound (e.g., base will deprotonate the phenol and increase solubility; strong reductants can affect the nitro group).
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Disposal: Collect as hazardous organic waste in accordance with institutional and local regulations.
Always consult the SDS for SKU N768896 for definitive safety, exposure limits, and emergency procedures.
Solvent Selection
Purpose: Efficient dissolution of niclosamide monohydrate for analytical stocks, screening solutions, or processing.
General solvent behavior (literature)
Polarity/ionization: Weakly acidic phenol (pKa ~6.5–7.5). Neutral form is highly lipophilic and poorly water‑soluble; phenolate salt (at basic pH) is much more water‑miscible.
Preferred solvents for neutral stocks: DMSO, DMF, NMP (typically enables 10–50 mM stocks at RT). Acetone, ethyl acetate, and MeCN show moderate solubility; EtOH/IPA can be used at elevated temperature or with sonication.
Aqueous media: Insoluble at neutral pH; dissolve first in DMSO, then dilute into buffered media (final DMSO ≤0.1–1% v/v for bioassays). Alternatively, adjust pH ≥8–9 to form the water‑soluble phenolate; note that pH shifts may affect downstream systems.
Practical guidance
For screening libraries: Prepare concentrated DMSO master stocks (e.g., 10–20 mM) and store aliquots at 2–8 °C or −20 °C to minimize freeze–thaw.
For analytical HPLC: Use MeCN/water with 0.1% formic acid or ammonium buffers; ensure column compatibility if sample is in DMSO.
Salt formation: Transient solubilization with mild base (e.g., Na2CO3) can aid aqueous processing; neutralize post‑dissolution if required.
Comparison (pros/cons)
DMSO: Highest solvating power; hygroscopic; can affect bioassays at >1%.
DMF/NMP: Strong solvents but less desirable toxicologically; consider handling controls.
Alcohols (EtOH/IPA): Greener profile, but limited achievable concentration.
Basic aqueous buffer: Green and inexpensive; may alter chemical state (phenolate) and UV/fluorescence properties.
Storage and Reconstitution
Storage (item-specific)
Temperature: Store at 2–8 °C (per Product Data).
Shipping: Shipped on wet ice to maintain cool conditions during transit.
Container: Keep tightly closed in original packaging; protect from light and excessive humidity to preserve hydrate state.
Reconstitution and solution handling (general guidance)
Solubility strategy: Prepare concentrated stocks in DMSO (e.g., 10–50 mM). For aqueous applications, dilute DMSO stocks into buffer with vigorous mixing; alternatively, dissolve under mildly basic conditions (pH 8–9) to form phenolate, if compatible.
Filtration: For analytical standards, pass solutions through 0.22 µm PTFE to remove particulates.
Aliquoting: Dispense single‑use aliquots to minimize freeze–thaw and moisture pickup; label with concentration, solvent, and preparation date.
Stability: Solid hydrates are generally stable refrigerated; solutions in DMSO are typically stable for weeks at 2–8 °C and months at −20 °C (literature guidance). Verify stability for your application by periodic HPLC.
Shelf life and specifications
Appearance, assay, water content, and related substances: Not specified for this item; refer to CoA/Spec Sheet.
Research use note
For research use only. Not for human or veterinary use.
Structure and Identity
Brief overview: Niclosamide monohydrate is the hydrated form of the chlorinated salicylanilide niclosamide. It contains a salicylamide core (o‑hydroxybenzamide) N‑acylated to a p‑nitro‑o‑chloroaniline, with an additional molecule of water of crystallization.
Item-specific identifiers (from Product Data)
SKU: N768896
Product name: Niclosamide monohydrate
CAS: 73360-56-2
InChIKey: 452864 (as provided; format appears truncated — verify against CoA/SDS)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (for reference; verify suitability for your work)
Core scaffold: salicylanilide bearing two chloro substituents (on each aryl ring) and one nitro substituent (on the aniline ring), plus an ortho-phenolic OH on the salicyl ring and a secondary amide linking the two rings.
Hydration state: monohydrate (one lattice H2O per niclosamide molecule).
Typical empirical formula (literature, monohydrate): C13H10Cl2N2O5 (niclosamide base C13H8Cl2N2O4 + H2O).
Ring systems: two para‑disubstituted benzene rings connected through an amide (–CONH–) bond.
Functional groups: phenolic OH ortho to amide on salicyl ring; nitro (–NO2) and chloro substituents on the anilide ring; two aryl chlorides; secondary amide; one molecule of lattice water.
Stereochemistry: achiral; planar conjugated salicylanilide framework with intramolecular H‑bonding (phenol O–H···O=C) commonly observed in salicylanilides (literature).
Synthetic Utility
Niclosamide monohydrate is a functionalized salicylanilide that can serve as a platform for analogue synthesis and as a test substrate in method development.
Functional group reactivity (literature)
Phenolic OH: Readily deprotonated; undergoes O‑alkylation/acylation (e.g., with alkyl halides or acid chlorides) under basic conditions (K2CO3/Cs2CO3) in polar aprotic solvents. Enables prodrug or solubility‑tuning derivatives.
Nitro group: Reducible to an aniline (Pd/C H2, Fe/AcOH, SnCl2), opening routes to further N‑acylation or cross‑coupling (after diazotization or via Buchwald–Hartwig from aryl halides if present).
Aryl chlorides: Potential handles for Pd‑catalyzed cross‑couplings (Suzuki–Miyaura, Buchwald–Hartwig after nitro reduction), allowing diversification on either ring.
Amide: Generally stable; can participate in H‑bond networks for cocrystal engineering.
Applications in synthesis and analysis
Test substrate for coupling/reduction optimization due to the coexistence of nitro, phenol, and aryl chloride functionalities (chemoselectivity challenges).
Precursor to labeled standards (e.g., 13C/15N or deuterated) by targeted transformations for bioanalytical LC–MS.
Scaffold for SAR: Systematic modification at O‑, N‑ (post‑reduction), and aryl positions to probe property relationships.
Considerations
Hydration state: KF analysis before stoichiometric use; dehydration can occur on heating or under vacuum.
Solubility management: Use strong polar aprotics or phase‑transfer catalysis; ensure exclusion of water for moisture‑sensitive coupling steps.
Target Specificity
Not applicable for this catalog item.
No antigen/epitope/clone/isotype information is associated with small-molecule Niclosamide monohydrate.
This section applies to biological affinity reagents (e.g., antibodies, proteins), not small molecules.
Preguntas frecuentes
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 73360-56-2, the molecular formula is C13H10Cl2N2O5. InChIKey ZBXRPLQCPHTHLM-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.
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