3-hydroxyquinolin-2(1H)-one - ≥98% , CAS No.26386-86-7

CAS: 26386-86-7 Cat. No.: H1071163 Summenformel: C₉H₇NO₂ Molekulargewicht: 161.16 EG-Nummer: 849-708-9 PubChem CID: 818159

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

C1=CC=C2C(=C1)C=C(C(=O)N2)O

IUPAC Name

3-hydroxy-1H-quinolin-2-one

InChIKey

BERPCVULMUPOER-UHFFFAOYSA-N

INCHI

1S/C9H7NO2/c11-8-5-6-3-1-2-4-7(6)10-9(8)12/h1-5,11H,(H,10,12)

Isomere SMILES

C1=CC=C2C(=C1)C=C(C(=O)N2)O

PubChem CID

818159

Molekulargewicht

161.16

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Quinolines and derivatives
      • Subclass Quinolones and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Quinolines and derivatives
• Subclass: Quinolones and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxyquinolones
• Alternative Parents: Hydroxyquinolines Hydroquinolones Hydroquinolines Pyridinones Hydroxypyridines Benzenoids Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydroxyquinolone - Dihydroquinolone - Hydroxyquinoline - Dihydroquinoline - Pyridinone - Hydroxypyridine - Benzenoid - Pyridine - Heteroaromatic compound - Lactam - Azacycle - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as hydroxyquinolones. These are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
• 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: 161.160 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 161.048 Da
• Monoisotopic Mass: 161.048 Da
• Topological Polar Surface Area: 49.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 235.000
• 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

There are no item-specific tested application protocols provided for this small molecule.

• General lab uses (illustrative; not validated for this SKU)
  • Stock solutions: prepare in dry DMSO or DMF at 10–100 mM for screening or photophysical studies; filter (0.22 μm) if needed.
  • Synthetic transformations: follow conditions outlined under Reaction Conditions and optimize to your substrate and scale.

Always validate conditions in your laboratory and consult the product’s CoA/SDS before use.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to primary literature if biological evaluation is planned.

• Literature/general perspective

  • Quinolinone frameworks occur in numerous natural products and research probes; 3‑hydroxy‑2‑quinolinone motifs are common in ESIPT fluorophores used to monitor microenvironments and hydrogen‑bond dynamics in vitro.
  • The scaffold is amenable to derivatization yielding libraries that have been screened against enzymes and receptors in chemical biology; however, no endogenous role is known for this specific compound.
  • Physicochemical profile (general): aromatic, H‑bond donor/acceptor, modest polarity; these features influence permeability and binding in target discovery campaigns, though specific targets are not assigned here.

All uses are strictly for research. No clinical/diagnostic claims are made.

Buffer Applications

This compound is not a conventional buffer component. It lacks a well‑defined, narrow pKa window paired to high aqueous solubility required for practical buffering systems.

• Practical note
  • For aqueous work, dissolve as a stock in DMSO/DMF or alcohols before dilution if compatible with your assay (general guidance), or derivatize to increase solubility.
  • For true buffering, select standard systems (e.g., phosphate, Tris, HEPES) appropriate to your pH range.

Green Alternatives

When planning synthesis or analytics with 3‑hydroxyquinolin‑2(1H)‑one, solvent choice and process conditions drive most of the environmental footprint.

• Greener solvent substitutions (literature guidance)

  • Replace DMF/DMSO in some O/N‑alkylations with Cyrene, propylene carbonate, or 2‑MeTHF where solubility permits.
  • Use ethanol or isopropanol for recrystallization instead of chlorinated solvents.
  • For extractions, prefer EtOAc/MTBE over DCM/CHCl3 when feasible.

• Small comparison (general)

  • DMF: high solvency but reproductive toxicity concerns; difficult to remove.
  • Cyrene/PC: lower toxicity profile; higher boiling points may demand energy for removal.
  • 2‑MeTHF: bio‑based, water‑immiscible; good for extractions; may give lower solubility for polar salts (phenoxides).

• Process intensification

  • Consider solvent‑free melt reactions for simple acylations if thermal stability allows.
  • Employ flow chemistry for hazardous reagents (e.g., alkyl halides) to reduce inventory and improve heat/mass transfer.

Note: Selections must be validated experimentally for this substrate’s solubility/reactivity; the above are general green-chemistry options, not item-specific specifications.

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; no pharmacopeial listing indicated.

• General R&D context (non-clinical)

  • 3‑Hydroxyquinolin‑2(1H)‑one serves as a heteroaromatic intermediate/scaffold in medicinal chemistry campaigns to prepare quinolinone and quinolone analogs for in vitro evaluation.
  • Roles are typically limited to synthetic intermediate or reference standard in discovery workflows (analytical characterization, SAR exploration), not as an excipient.
  • Manufacturing relevance: none specific; any scale‑up would follow standard GMP controls for intermediates if used in regulated routes, but this product is supplied for research use only.

Physical Properties

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: 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.
  • Melting point, boiling point, density, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties (for reference; not item specifications)

  • Empirical formula: C9H7NO2 (literature)
  • Formula weight: ~161.16 g/mol (literature)
  • Physical state: typically a crystalline solid for quinolinone derivatives (literature trend)
  • Solubility profile: limited aqueous solubility expected; soluble in polar aprotic organics (DMSO, DMF) and moderately in alcohols/acetone upon heating (literature trends for quinolinones)
  • Acid/base behavior: weakly acidic phenol (pKa of phenolic OH in related systems ~9–10) and weakly basic lactam (typically nonbasic) with potential for intramolecular H‑bonding; overall amphiprotic character (general quinolinone behavior)
  • Spectroscopic features: strong C=O stretch near 1660–1700 cm⁻¹ and phenolic O–H in IR; UV absorption in near‑UV due to conjugated quinolinone chromophore (literature)

Note: Exact numeric values for this SKU are not established here and should be taken from the product’s CoA/SDS where available.

Quality and Grades

• Item-specific grade/purity

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

• Guidance on grades (general)

  • Research-grade heteroaromatic solids are typically supplied with an assay (e.g., HPLC/GC) and limits for common impurities (solvents, inorganic ash). When UV transparency is critical (analytical photophysics), low-UV grade or spectral grade solvents are used for measurements rather than relying on solid purity.
  • Stabilizers: Not typically required for quinolinone solids; none are specified for this item. If stabilizers were present, they can influence downstream reactions (e.g., phenolic alkylations) and should be removed during workup.
  • Trace analysis: If metals or residual halides matter (e.g., for catalytic studies or photophysics), request CoA including elemental analysis and residual solvent data.

• Batch-to-batch considerations (general best practice)

  • Confirm polymorph/solvate state by PXRD or DSC if crystallinity impacts performance (e.g., fluorescence or recrystallization behavior).
  • Verify water content (Karl Fischer) when exact stoichiometry or reactivity depends on dryness; no item-specific water content is provided here.

Reaction and Applications

• Research/manufacturer note

  • Research Use: For research use only (per Product Data). No clinical/diagnostic applications.

• Literature applications (general; not item-specific claims)

  • Scaffold for quinolinone/quinolone libraries: the 3‑hydroxy group and 2‑lactam enable diverse derivatization (ethers, esters, carbamates, N‑alkyl/amides) for SAR studies in chemical biology and materials.
  • ESIPT fluorophore core: 3‑hydroxy‑2‑quinolinone motifs exhibit excited‑state intramolecular proton transfer (ESIPT), enabling dual emission and large Stokes shifts; derivatives are used in probes and solid‑state emitters.
  • Metal chelation: O,O/N,O‑binding to transition metals affords coordination complexes used to probe photophysics and catalysis.

• Practical reactivity features

  • Phenolic O‑alkylation/acylation: base (K2CO3, Cs2CO3) in DMF/acetone for SN2 alkylation; acyl chlorides/anhydrides afford esters.
  • Lactam N‑functionalization: stronger base (NaH, K2CO3 with phase transfer) enables N‑alkylation or N‑acylation; selectivity O vs N can be tuned by base/solvent.
  • Cross‑coupling after halogenation: electrophilic halogenation on the ring (e.g., 6‑/7‑positions in quinolinone series) provides handles for Suzuki/ Buchwald reactions.
  • Protection strategies: O‑silylation (TBDMS/TBSCl, imidazole) to mask the phenol during N‑acylation.

• Workup tips

  • Quench strong bases carefully; neutralize to avoid lactam ring opening (rare). Use acidic aqueous washes to remove inorganic bases and drive reprotonation, then recrystallize.

Reaction Conditions

The following are literature-style, general conditions for this scaffold; they are not item-specific specifications.

• O‑Alkylation (phenolic)

  • Typical: 1.1–2.0 eq alkyl halide (primary), 1.5–3.0 eq K2CO3 or Cs2CO3, DMF or acetone, 25–60 °C, 2–16 h; inert atmosphere optional. Workup by aqueous quench and extraction; purification by column or recrystallization.

• O‑Acylation

  • Acyl chloride/anhydride (1.1–1.5 eq), base (Et3N or pyridine), DCM/MeCN, 0 °C to rt, 1–4 h. Monitor for competitive N‑acylation; control by base and temperature.

• N‑Alkylation (lactam)

  • NaH (60% dispersion, 1.1–1.5 eq) or K2CO3/Cs2CO3 (2–3 eq) with phase-transfer catalyst, DMF/DMSO/MeCN, 0–25 °C to reflux, 2–18 h. Selectivity tuned via protecting groups and solvent polarity.

• Electrophilic halogenation of the ring

  • NBS/NCS (1.0–1.2 eq), catalytic acid, AcOH or DMF, 0–25 °C; regioselectivity depends on substitution and directing effects; isolate halogenated intermediates for cross‑coupling.

• Cross‑coupling (after aryl halide installation)

  • Suzuki–Miyaura: Pd(PPh3)4 or Pd2(dba)3/XPhos, base (K2CO3/K3PO4), dioxane/H2O or toluene, 60–100 °C, 4–24 h.
  • Buchwald–Hartwig (for N‑arylation on suitable derivatives): Pd catalysts, BINAP/XPhos, NaOtBu, toluene/1,4‑dioxane, 80–110 °C.

• Analytical

  • HPLC: reversed‑phase C18 with aqueous buffer/MeCN gradients; detect near 254–330 nm (chromophore present). Adjust pH to suppress ionization for sharper peaks.

Safety and Handling

• Item-specific hazard data

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

• General laboratory safety guidance for quinolinone solids (literature/standard practice)

  • PPE: wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dusts.
  • Handling: avoid generating dust; minimize skin/eye contact. Weigh with local exhaust ventilation.
  • Storage: per Product Data, store at room temperature. Keep in a tightly closed container, protected from moisture and strong oxidizers/bases.
  • Incompatibilities: strong oxidizing agents, strong bases (can promote O/N‑deprotonation and undesired reactions), and strong acids for prolonged contact.
  • Thermal stability: aromatic lactams are generally thermally stable solids; avoid excessive heating without characterization.

• First aid (overview; defer to SDS for authoritative instructions)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for ≥15 minutes; remove contaminated clothing; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting unless directed; seek medical attention.

• Environmental considerations (general)

  • Prevent release to the environment. Collect solid waste and contaminated disposables in labeled containers for hazardous disposal per institutional and local regulations.

Solvent Selection

This compound is a heteroaromatic lactam/phenol. Solvent choice is typically driven by the operation (synthesis vs. analytics) and desired ionization state.

• General miscibility/solubility trends (literature; not item-specific specs)

  • Good: DMSO, DMF, NMP; moderate in acetone, MeCN, alcohols (MeOH/EtOH) on warming; limited in nonpolar solvents (toluene/hexanes); low in water.
  • Ionization aids: addition of base (K2CO3, NaH) can deprotonate O–H/N–H to increase solubility in polar aprotics for O/N‑alkylation.

• Use-case guidance

  • Reaction medium: polar aprotic solvents (DMF, DMSO, DMAc) facilitate SN2 O‑ and N‑alkylations; MeCN or acetone for acylations with bases.
  • Purification: recrystallization from alcohols (EtOH/i‑PrOH) or binary systems (EtOAc/hexanes) is common for quinolinones; adjust to solubility.
  • Spectroscopy/photophysics: use spectroscopic‑grade solvents (MeCN, EtOH, 2‑MeTHF) to minimize background.

• Comparisons

  • DMF vs DMSO: DMF often gives cleaner workups for alkylations; DMSO offers higher solubility but can complicate isolation.
  • Alcohols vs aprotics: alcohols are greener but may compete in acyl transfer; aprotics offer stronger solubilization of phenoxide/lactamate.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance

  • Keep container tightly closed, in a dry place, protected from light and moisture. Use desiccation if long-term storage is planned.
  • Avoid prolonged exposure to strong bases/acids in storage to prevent degradation or salt formation.

• Reconstitution/solution preparation (literature-based guidance)

  • Solvents: DMSO, DMF, or alcohols are commonly used to prepare concentrated stocks; warm gently and sonicate if needed.
  • Filtration: sterile-filter solutions (0.22 μm PTFE) for assay use if appropriate.
  • Stability: Prepare fresh solutions when possible; for extended storage, aliquot and freeze solutions compatible with the solvent (check freezing point and container compatibility). Avoid repeated freeze–thaw cycles by aliquoting.

Refer to the CoA/SDS for any item-specific stability or incompatibility information not listed here.

Structure and Identity

A heteroaromatic lactam belonging to the quinolinone family; 3‑hydroxyquinolin‑2(1H)‑one bears a phenolic OH at C‑3 and a 2‑lactam (1H‑quinolin‑2‑one) core capable of keto–enol/amide–iminol tautomerism.

• Item-specific identifiers (Product Data)

  • SKU: H1071163
  • Product Name: 3-hydroxyquinolin-2(1H)-one
  • CAS: 26386-86-7
  • CID: 818159
  • InChIKey: 22867 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (non-item-specific; for reference only)

  • Common synonyms: 3-hydroxy-2-quinolinone; 3-hydroxycarbostyril (tautomeric nomenclature)
  • Molecular formula (literature): C9H7NO2
  • Molecular weight (literature): ~161.16 g/mol
  • Functional groups: fused benzannulated pyridone (quinolin-2-one), phenolic OH at C-3, lactam NH
  • Tautomerism: 2‑pyridone ↔ 2‑hydroxypyridine (here, quinolinone ↔ hydroxyquinoline) with intramolecular H‑bonding potential (ESIPT‑active scaffolds)

• 2D structural description (general)

  • A bicyclic system composed of a benzene ring fused to a 2‑pyridone. The lactam carbonyl resides at the quinoline 2‑position, the ring nitrogen is adjacent (1‑position, protonated in the 1H‑lactam form), and a phenolic OH is at the 3‑position ortho to the carbonyl, enabling strong intramolecular O–H···O=C hydrogen bonding.

Synthetic Utility

• Functional handles

  • Phenolic OH (C‑3): enables O‑alkylation, O‑acylation, carbonate/carbamate formation, Mitsunobu etherification with primary alcohols.
  • Lactam NH (1‑position): allows N‑alkylation/acylation, formation of N‑oxide (after oxidation at ring N in related quinolines), and participation in H‑bonding templates.
  • Aromatic ring: electrophilic substitution (nitration/sulfonylation/halogenation) guided by the lactam/phenol directing effects; late‑stage cross‑coupling after halogenation.

• Retrosynthetic value

  • Entry point to quinolinone libraries: downstream diversification via O/N functionalization followed by Suzuki/Buchwald couplings on halogenated derivatives.
  • Protecting group logic: temporary O‑silylation (TBS) to bias N‑acylation; conversely, N‑Boc protection (if applicable) to direct O‑functionalization.

• Derivatization map (examples; literature)

  • Ether series: K2CO3, alkyl halide, DMF → 3‑alkoxyquinolin‑2‑ones.
  • Ester series: acyl chloride/anhydride, base, Et3N or pyridine → 3‑O‑acyl products; subsequent Fries‑type rearrangements possible under strong conditions.
  • N‑alkyl series: NaH, alkyl halide, THF/DMF → N‑alkyl quinolin‑2‑ones; influences tautomerism and photophysics.
  • Metal complexes: deprotonated O/N donors chelate to Zn(II), Al(III), etc., affording emissive complexes (materials research).

Target Specificity

No biological target specificity data are provided for this product.

• Item-specific fields
  • Antigen/epitope/clone/isotype/species reactivity: Not applicable; this is a small molecule heterocycle, not an antibody or biologic.

For any target-binding studies, consult primary literature and perform de novo characterization.