This compound belongs to the class of organic compounds known as hydroxyquinolines. These are compounds containing a quinoline moiety bearing a hydroxyl 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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
202.210 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
202.074 Da
Monoisotopic Mass
202.074 Da
Topological Polar Surface Area
62.200 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
245.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent, and none are provided in the Product Data.
General usage examples (research context)
Stock solution preparation: Dissolve in dry DMSO at 10–50 mM; store aliquots to avoid repeated freeze–thaw (see Storage & Reconstitution).
Metal-binding assay: Prepare ligand solution in MeOH/H2O or buffer; adjust pH; titrate metal salt while monitoring UV–Vis/fluorescence to obtain binding isotherms.
O‑alkylation setup: Suspend in dry DMF with base (e.g., K2CO3), add alkyl halide, stir under N2, and monitor by TLC/HPLC.
These are illustrative, literature-style examples; optimize for your system and consult primary references for detailed procedures.
Biological Roles
No item-specific biological data are provided. The following notes are general to 8‑hydroxyquinoline-type chemotypes and are not clinical claims.
Metal-binding motif
The 8‑hydroxyquinoline scaffold is a recognized O,N‑bidentate chelator. Such ligands can modulate availability of biologically relevant metal ions (e.g., Zn2+, Cu2+, Fe3+) in vitro, affecting metalloenzyme activity in research models.
Physicochemical considerations
The presence of both a phenolic OH and an amide confers hydrogen-bonding capacity and intermediate lipophilicity, which may influence membrane association and protein binding in biochemical assays.
Assay implications (research context)
Chelation can confound metalloprotein assays, ROS generation assays (via Fenton-like chemistry if redox-active metals are present), and fluorescence-based readouts (due to intrinsic chromophore/complex emission). Appropriate metal-free controls are recommended.
Metabolic liabilities (general expectations)
Phase II conjugation (glucuronidation/sulfation) of the phenol and hydrolysis of the amide under enzymatic or extreme pH conditions can occur in biological matrices (literature precedent for phenolic amides), potentially altering activity/fluorescence.
For any use in biological systems, this product is for research use only; verify purity, endotoxin levels (if relevant), and solvent vehicle compatibility before experimentation.
Buffer Applications
This compound is not a dedicated buffering reagent. It does not constitute a classical buffer system with a defined pKa window and high buffer capacity in water.
Practical notes
If dissolved into biological buffers (HEPES, PBS, Tris) for assays, maintain low cosolvent fractions (e.g., ≤1–2% DMSO) and confirm that the working buffer pH does not induce undesired deprotonation (phenoxide formation) unless intended for metal-binding studies.
For metal-complexation experiments, carbonate or borate buffers at basic pH can assist in generating the phenoxide, but be mindful that buffer anions can also coordinate metals and compete with the ligand.
Green Alternatives
Considerations below are general and intended to help select more sustainable options or conditions when the precise properties of this item are not yet established.
Functional role alternatives
Metal chelation: For aqueous processes, biodegradable polycarboxylates (e.g., citrate, gluconate) or EDDS may be greener than hydrophobic heteroaromatics; they trade off photophysical reporting and selectivity.
Sensing/reporting: Water-soluble salicylate or catechol-based probes can reduce reliance on high-boiling dipolar aprotic solvents, but may provide weaker or less selective binding vs quinolinol systems.
Solvent/condition choices for this compound
Prefer ethanol, isopropanol, or ethyl acetate for workup/purification when feasible. Use water/EtOH mixtures for complexation studies to reduce DMSO/DMF usage.
Base selection: K2CO3 or Na2CO3 in green solvents (EtOH, 2‑MeTHF) for O‑acyl/alkyl reactions when compatible; avoid strong bases in DMF/DMSO where waste treatment is burdensome.
Comparison snapshot (general)
8‑hydroxyquinoline derivatives vs polyaminocarboxylates
Pros: strong, tunable O,N chelation; photophysical readouts; lipophilicity aids extraction.
Catechols, hydroxypyridinones (HPOs), and amino acid-based ligands offer improved aqueous handling; selectivity/signal properties may differ.
Adopt microscale screening and solvent recycling to minimize environmental footprint regardless of ligand choice.
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided for this item. It is supplied for research use only.
General context (non-clinical)
8‑Hydroxyquinoline derivatives are used in research as metal-binding motifs and fluorescence reporters. In formulation R&D contexts, such aromatic heterocycles may be explored as analytical reagents or tracers rather than as functional excipients.
Considerations for formulation research (if applicable)
Solubility enhancement may require DMSO, ethanol, or cyclodextrins; verify stability versus pH and light.
Avoid unintended metal contamination in formulation equipment, as chelation can alter apparent solubility and assay signals.
Any application in human or veterinary products requires separate qualification and is outside the scope of this research-use-only listing.
Physical Properties
Item-specific specifications are not provided in the Product Data; consult CoA/Spec Sheet for definitive values.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~202.21 g/mol (computed from formula C11H10N2O2; literature/computed, not a product spec)
Molecular formula: C11H10N2O2 (derived from the name; literature/computed)
Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general expectations; literature/experience, not product spec)
Likely soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP) and moderately in alcohols (MeOH, EtOH).
Limited solubility in water at neutral pH; aqueous solubility increases under basic conditions due to deprotonation of the phenolic OH to the phenoxide.
Acid–base properties (literature trends for 8‑hydroxyquinoline analogs)
Phenolic OH pKa typically ~9–10; substitution at C-2 can slightly shift this value.
Amide N–H is a very weak acid (pKa ≤ 1 in DMSO scale context; essentially non-ionizable in water) and not appreciably basic.
Partitioning (qualitative)
Aromatic heterocycle with a phenol and an amide suggests amphipathic character (intermediate polarity), often facilitating extraction into medium‑polarity organic solvents.
For measured, item-specific physicochemical data (mp, assay format solubility limits, water content, residual solvents), refer to the item’s CoA/Spec Sheet.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
What grade means in practice (general context)
Research grade fine chemicals are typically suitable for synthetic, analytical, and materials research. Where applicable, enhanced grades (e.g., HPLC, LC–MS) focus on low UV background, low metal content, and minimal volatiles that interfere with high-sensitivity detection. In absence of a declared grade, assume standard research-use quality and verify suitability by small-scale trials.
Stabilizers/inhibitors: None specified for this item. If ultra-low metal background is required (e.g., for metal-catalyzed cross-couplings sensitive to chelators), consider pre-washing glassware and avoiding contact with reactive metals given the ligand character of the 8‑hydroxyquinoline core.
What to check on the CoA/Spec Sheet (practical tips)
Identity confirmation (NMR, HRMS or LC–MS retention match), assay purity (area % by HPLC/GC), residual solvents, and water content (Karl Fischer) if relevant to your application.
If using for photophysical studies, review UV–Vis/fluorescence background and impurity profile; the 8‑hydroxyquinoline chromophore can have significant absorbance in the near‑UV.
For regulated or analytical workflows, use the specific CoA lot data to set acceptance criteria.
Reaction and Applications
Coordination/analytical chemistry (literature)
The 8‑hydroxyquinoline (oxine) core is a classic O,N‑bidentate chelator. Even with 2‑substitution, many metal ions (e.g., Al3+, Zn2+, Cu2+, Ga3+) can form complexes via the phenoxide oxygen and the ring nitrogen. These complexes are often colored/fluorescent and used for photophysical studies, ion sensing, and extraction.
Derivatization chemistry (general)
Phenolic OH: amenable to O‑alkylation (Williamson-type), O‑acylation, and carbonate/carbamate formation. Protecting groups (e.g., benzyl, silyl) can be installed/removed under standard conditions.
Amide N–H: weakly nucleophilic; can be deprotonated with strong base and further acylated or alkylated under forcing conditions, though resonance reduces reactivity. Hydrogen-bonding enables supramolecular assembly and crystal engineering.
Aromatic ring: electrophilic substitution (nitration/sulfonation/halogenation) is guided by the heteroatom pattern; positions 5 and 7 are commonly accessible on 8‑hydroxyquinoline frameworks (literature precedent), though 2‑substitution introduces steric/electronic effects.
Materials and sensing (literature)
8‑Hydroxyquinoline derivatives are frequently employed in OLED emitter/host development (e.g., Alq3 analogs), chemosensors, and metal ion extractants. N‑acylation at C‑2 can tune solubility, photophysics, and binding constants.
Practical tips
For chelation work, adjust pH to deprotonate the phenol (pH ≥ 8–10) to favor complexation; monitor by UV–Vis/fluorescence.
For O‑functionalization, ensure anhydrous conditions and use bases such as K2CO3, Cs2CO3, or NaH with appropriate alkylating agents; avoid metal counterions that could sequester the ligand.
Metal contaminants can bind strongly; use metal-free glassware and salt-free reagents for kinetic/thermodynamic measurements.
Reaction Conditions
General conditions below are drawn from literature precedents for 8‑hydroxyquinoline derivatives and phenolic amides; they are guidance, not product specifications.
O‑Alkylation of the phenol
Base: K2CO3 or Cs2CO3 (1.5–2.5 equiv) in dry DMF or acetone; alkyl halide (1.2–2.0 equiv).
Temperature: 25–60 °C (room temp for reactive benzyl/allyl halides; gentle heat for primary alkyl bromides/iodides).
Time: 1–16 h depending on electrophile.
Notes: Exclude moisture; avoid metal salts that could chelate the substrate and suppress reactivity.
O‑Acylation/Carbonate formation
Reagents: acyl chlorides or chloroformates (1.2–1.5 equiv), base (Et3N, pyridine) in DCM/THF at 0–25 °C.
Monitoring: TLC/HPLC with UV detection; quench and wash with aqueous bicarbonate.
Complexation with metal salts
Metals: Al3+, Zn2+, Cu2+, Ga3+ (typical for 8‑hydroxyquinoline).
Solvent: EtOH/MeOH or MeOH/H2O mixtures; adjust pH to 8–10 to form phenoxide.
Stoichiometry: often 3:1 ligand:metal for Al(III) (literature, e.g., Alq3‑type complexes), but depends on metal and sterics at C‑2.
Conditions: Nitration (AcOH/HNO3, 0–5 °C), halogenation (NBS/NCS in DMF/AcOH); regioselectivity influenced by 8‑OH and 2‑amide.
Always run small-scale trials and adjust equivalents/temperatures based on reactivity of your specific substrates and desired selectivity.
Safety and Handling
GHS/CLP status: Not specified in Product Data. Always consult the SDS for authoritative hazard classification, precautionary (P) statements, and regulatory details.
Anticipated hazards (general for phenolic/amide aromatic heterocycles; not product-specific):
May cause skin and eye irritation; avoid inhalation of dusts. Use in a fume hood to minimize exposure.
Phenolic compounds can be harmful if ingested and may cause respiratory irritation as dusts.
PPE and engineering controls (good laboratory practice)
Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders carefully to avoid aerosolization. Work in a chemical fume hood.
Incompatibilities and reactivity (general guidance)
Avoid strong oxidizers.
Strong bases can deprotonate the phenol (forming phenoxide) and may promote O‑alkylation/esterification; strong acids/bases can catalyze amide hydrolysis under forcing conditions.
The 8‑hydroxyquinoline motif is a known metal chelator; avoid contact with metal salts if chelation is undesirable in your process.
First aid (overview; defer to SDS)
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety
Organic solid; use water spray, CO2, dry chemical, or foam. Combustion may produce oxides of carbon and nitrogen; firefighters should wear self-contained breathing apparatus.
Always consult the product SDS for definitive hazard, handling, and disposal guidance.
Solvent Selection
Given its aromatic heterocycle plus phenol and amide, N-(8-hydroxyquinolin-2-yl)acetamide typically dissolves best in polar aprotic organic solvents and moderately in polar protic solvents.
Preferred: DMSO, DMF, NMP (high solubility for stocks and reactions); also acetone, acetonitrile to moderate levels.
Protic solvents: methanol, ethanol often adequate; isopropanol less effective.
Aqueous media: limited solubility at neutral pH; basic aqueous solutions increase solubility via phenoxide formation. Buffers above pH ~10 can increase dissolution but may alter coordination/photophysics.
When to choose which solvent
For spectroscopy or bioassay stock solutions: DMSO is typical due to high solvency and compatibility with dilution into aqueous buffers (≤1–2% v/v DMSO final).
For O‑alkylation/esterification of the phenol: use dry polar aprotic solvents (DMF, DMSO, acetone) with appropriate bases.
For metal complexation studies: ethanol, methanol, or mixed MeOH/H2O under controlled pH are commonly used to manage chelation equilibria and spectral readouts.
Comparison notes (general)
DMSO vs DMF: DMSO offers higher solvency and is less volatile; DMF may be preferred for some base-promoted transformations due to lower nucleophilicity of the medium.
Alcohols vs aprotics: alcohols can hydrogen-bond to the phenol/amide, slightly modulating acid–base/chelation properties; aprotics give cleaner control over deprotonation equilibria.
Always dry aprotic solvents when base-sensitive transformations are planned; water can suppress phenoxide generation and reduce reaction rates.
Storage and Reconstitution
Storage conditions (from Product Data)
Store at room temperature.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Stability considerations (general)
Keep container tightly closed in a dry, well‑ventilated place. Protect from strong light and moisture. Avoid prolonged exposure to basic vapors to prevent slow O‑alkylation or surface reactions.
Phenolic/amide aromatic solids are typically stable for months to years when protected from moisture and heat; verify by periodic HPLC.
Reconstitution and stock solutions (general lab guidance)
For synthetic use: Prepare concentrated stocks in anhydrous DMSO, DMF, or NMP (e.g., 10–50 mM). Filter if particulates remain. Record exact concentration gravimetrically where precision is required.
For assay use: Dilute DMSO stocks into buffer with vigorous mixing to avoid precipitation; keep final DMSO ≤1–2% v/v for cell-free assays. For aqueous-only work, adjust pH to slightly basic to aid dissolution (noting potential effects on chelation/photophysics).
Aliquot stocks and store sealed under inert gas if long-term storage is planned; avoid repeated freeze–thaw.
Disposal
Dispose of unused material and solutions in accordance with institutional and local regulations for organic laboratory chemicals; chelating ligands may require special consideration to avoid mobilizing heavy metals in waste streams.
For any item-specific stability or reconstitution instructions, defer to the lot-specific CoA/Spec Sheet.
Structure and Identity
Brief description: N-(8-hydroxyquinolin-2-yl)acetamide is an aromatic acetanilide-type derivative of 8‑hydroxyquinoline, featuring a phenolic OH at the 8-position and an N‑acetyl substituent bound at the quinoline 2‑position.
Product identifiers (from Product Data)
SKU: N1035995
CAS: 312591-57-4
PubChem CID: 1380881
InChIKey (as listed): 204985 (note: this appears truncated vs typical InChIKeys; consult CoA/SDS for the definitive identifier)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general description; based on the chemical name)
Core ring system: quinoline (benzopyridine) with the ring nitrogen at position 1.
Substituents: phenolic OH at C-8; N-acetyl anilide linkage at C-2 (the amide nitrogen forms a C–N bond to the C-2 of quinoline, and bears an acyl substituent CH3–CO–).
2D structure in words: a fused bicyclic aromatic system (benzene fused to pyridine) with an –OH para to the ring junction on the benzene portion (position 8) and an anilide –NH–C(=O)–CH3 substituent attached at the 2‑position adjacent to the ring nitrogen.
Molecular formula and mass (computed/literature, not product specification)
Calculated formula: C11H10N2O2 (based on the described connectivity)
Note: Where exact identifiers or structures are required for regulated reporting, defer to the item’s CoA/Spec Sheet.
Synthetic Utility
Functional-group leverage
Phenolic OH: platform for O‑alkyl, O‑acyl, or carbonate installation to tune lipophilicity and electronic properties; can be converted to leaving groups (e.g., triflates) for cross-coupling on the aromatic ring (literature precedent on phenolic heteroarenes).
Amide N–H: though deactivated, it can be further derivatized (N‑acylation/alkylation) or engaged in hydrogen-bonding to direct supramolecular assembly/crystallization.
Quinoline core: supports electrophilic substitution and metal-catalyzed C–H activation strategies; the 2‑substitution and 8‑OH guide regioselectivity.
Ligand and complex precursor
Retains the hallmark O,N chelation of 8‑hydroxyquinoline, enabling synthesis of metal complexes for catalysis or photophysics (e.g., Al, Zn, Cu complexes with modulated emission compared to oxine itself).
Retrosynthetic role
Serves as a protected/functionalized 8‑hydroxyquinolinyl synthon where the 2‑position is fixed as an anilide; downstream transformations can target positions 5/7 or the phenol.
Purification and analytics
Aromatic character affords strong UV (near‑UV) absorbance for HPLC monitoring. Metal binding can cause tailing; include EDTA in mobile phases if chelation to trace metals affects chromatography.
Overall, the combination of a phenol, an amide, and a heteroaromatic nucleus makes this a versatile intermediate for ligand development and functional materials.
Target Specificity
Not applicable for this small-molecule research chemical. No antibody/biological target specificity is provided in the Product Data. If used as a ligand or probe in biochemical assays, any “specificity” will derive from coordination preferences (e.g., for certain metal ions) rather than a biological epitope or protein target.
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