This compound belongs to the class of organic compounds known as hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.
External Descriptors
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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.
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Application Protocols
No biological assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block, and none are provided in the Product Data.
General lab usage tips (chemistry-focused):
Prepare concentrated stock solutions in dry DMSO or DMF for parallel synthesis or screening; filter if particulates are present.
For cross-couplings, pre-dissolve the heteroaryl substrate in the reaction solvent under inert atmosphere before base addition to minimize salt precipitation.
Validate identity/purity by 1H/13C NMR and HRMS; for phenolic compounds, consider recording spectra in dry, basic, and acidic conditions to probe tautomerism.
For any biological application development, users must devise and validate their own protocols; this product is for research use only.
Biological Roles
No biological roles are specified for this item. The following are general, literature-based observations for quinolinols; they do not imply suitability for any biological or clinical use.
Structural motif: Quinolinols (and their keto tautomers, quinolinones) frequently serve as scaffolds in chemical biology probes and as ligating units for metal-binding motifs in research settings.
Tautomerism: The 2-hydroxy/2-quinolinone equilibrium can modulate hydrogen-bond donor/acceptor patterns and influence interactions with biomacromolecules in biophysical studies (e.g., binding assays, fluorescence quenching), strictly for in vitro research.
Metal coordination: N,O-donor sets can chelate transition metals; 7-substitution tunes electronic properties, which is relevant when designing research probes for sensing or catalysis-mimetic systems.
Photophysics: Conjugated heteroaromatic systems may exhibit UV fluorescence with solvent/pH dependence (literature), useful for analytical tracer studies.
Important: This product is labeled For research use only and is not intended for diagnostic, therapeutic, or in vivo applications.
Buffer Applications
This compound is a hydrophobic heteroaromatic building block and is not typically used as a buffering agent. It lacks a conjugate acid/base pair with a suitable, sharply defined pKa window and adequate aqueous solubility to function as a practical buffer.
For aqueous work, dissolve only as a research analyte/ligand in mixed organic/aqueous media (e.g., DMSO cosolvent) rather than as a buffering component.
Refer instead to the Reaction & Applications and Synthetic Utility sections for relevant uses.
Green Alternatives
Greenness can be improved via solvent/catalyst selection and by leveraging the aryl chloride handle effectively.
Strategies (literature/guidance):
Solvent substitution:
Replace DMF/NMP with EtOH/H2O, MeCN/H2O, 2-MeTHF, or CPME where feasible in couplings or O-alkylations.
For Suzuki couplings, aqueous ethanol or water/dioxane mixtures often work with modern Pd catalysts.
Catalysis choices:
Use highly active ligand systems (e.g., XPhos/BrettPhos, Pd-PEPPSI for NHCs) enabling lower catalyst loadings and milder temperatures, improving E-factor.
Explore Ni-catalyzed couplings to avoid Pd where downstream metal removal is constrained (tradeoff: substrate scope/sensitivity).
Base/conditioning:
Replace strong, hazardous bases (NaH) with milder carbonates/alkoxides when compatible; consider mechanochemistry (ball milling) for O-alkylations to reduce solvent use (emerging literature).
Energy:
Employ microwave or flow chemistry to shorten reaction times and enhance heat transfer, reducing energy consumption.
Comparison snapshot (literature, typical trends):
DMF vs 2-MeTHF: 2-MeTHF is bio-based, lower toxicity, easier workup; DMF offers superior solvation but poorer environmental profile.
Toluene vs CPME: CPME has broader stability, lower peroxide formation than THF/Et2O, and favorable azeotrope behavior; toluene is widely available but higher VOC impact.
Note: Substrate-specific reactivity may necessitate traditional solvents; validate greener swaps on small scale first.
Pharmaceutical Uses
No pharmacopeial/excipient status or formulation role is specified for this item; refer to CoA/Spec Sheet. The notes below are general, literature-based and do not constitute medical or clinical claims.
Role in development chemistry: 7-chloro-2-hydroxyquinoline can serve as an intermediate for discovery-scale synthesis, enabling rapid diversification via cross-coupling at C-7 and O-functionalization at C-2.
Process considerations (research context):
Avoid residual palladium/nickel above internal limits following couplings; consider metal scavengers or carbon treatment.
Control polymorphism/solid form for reproducible handling; quinolinols may display different crystallization habits depending on solvent system (literature).
Regulatory: Not listed here as USP/EP/JPE monograph material. Any use in GMP contexts would require independent qualification and full impurity profiling.
Physical Properties
Item-specific physico-chemical specifications are not provided in the Product Data. The following are typical literature values/general characteristics for 7-chloro-2-hydroxyquinoline; they are NOT product specifications.
State/appearance: Solid; color not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~179.60 g/mol (literature, for C9H6ClNO)
pKa: Phenolic OH in 2-hydroxyquinoline typically pKa ~9–10; tautomeric 2-quinolinone conjugate acid pKaH ~–1 to 1 (literature, varies with substitution).
Solubility (qualitative, literature):
Water: low to sparingly soluble due to hydrophobic quinoline core
Organic: soluble in polar organics (DMSO, DMF, NMP); moderate in alcohols and chlorinated solvents; limited in nonpolar hydrocarbons
LogP/logD: Quinolinols often exhibit logP ~1.5–2.5; chloro substitution increases lipophilicity (literature trend, not a spec).
UV–Vis: Conjugated heteroaromatic; strong absorbance in near-UV (around 240–330 nm, literature for quinolinols; exact λmax depends on solvent/tautomer).
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Notes: The 2-hydroxy/2-quinolinone tautomer ratio depends on solvent polarity and hydrogen-bonding capacity, influencing spectroscopic and acid–base properties (literature). Drying before use can improve reproducibility in base-sensitive transformations.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. Without a stated grade, users should verify suitability for sensitive applications (e.g., trace-metal catalysis, photophysics) via the supplied CoA or in-house QC.
Guidance on common grades (general information):
Research/technical grade: Suitable for most synthetic transformations; may have higher levels of UV-active or inorganic impurities.
Purified/98%+: Typical for small-molecule building blocks; generally fine for cross-coupling and O-derivatization. Confirm residual halides, water, and trace metals as needed (analytical HPLC/GC, KF, ICP-MS), if critical to your workflow.
HPLC grade (for solvents) and spectroscopy grade are not applicable here; this is a solid building block rather than a solvent.
Stabilizers/Inhibitors: None specified for this item; refer to CoA/Spec Sheet. Quinolinols typically do not require stabilizers; however, adventitious oxidation or esterification of the phenol under improper storage can occur (literature observation). Verify identity/purity by NMR and MS upon receipt for quantitative work or SAR studies.
Reaction & Applications
As a chloro-substituted quinolinol, this reagent is a versatile intermediate for assembling N-heteroaromatic frameworks and ligand-like motifs.
Key application families (literature):
Cross-couplings at C-7 (aryl chloride handle):
Suzuki–Miyaura: coupling with boronic acids/esters to diversify the arene; Pd(dppf)Cl2 or Pd/XPhos, K3PO4 or K2CO3, dioxane/H2O, 80–100 °C.
Buchwald–Hartwig amination: install anilines/alkyl amines; Pd2(dba)3 or Pd(OAc)2 with BrettPhos/SPhos, NaOtBu or Cs2CO3, toluene or dioxane, 90–110 °C.
Sonogashira: terminal alkynes; Pd/Cu co-catalysis, Et3N or i-Pr2NH base, toluene/Et3N or DMF, 60–90 °C.
Negishi/Kumada: via Mg or Zn organometallics where compatible with the phenol (often protected as an ether or managed by base choice).
Phenolic O-functionalization at C-2:
O-alkylation/acylation: K2CO3/Cs2CO3 or NaH, MeCN/DMF; affords ethers/esters as protecting groups or functional handles.
Carbonyl chemistry via tautomer (2-quinolinone): N-acylation and subsequent transformations possible depending on tautomeric control.
Directed metalation/orthogonalization:
The phenoxide can direct ortho-metalation or chelate to metals, enabling C–H activation protocols (literature).
Coordination/analytical uses (literature):
Quinolinol motifs bind metal ions; 7-substitution allows tuning of photophysical and binding properties for chemosensors or materials precursors (non-clinical, research context).
Practical tips: Dry conditions benefit cross-couplings; consider protecting the OH if it deactivates catalysts or competes for base (e.g., methyl/benzyl ether) when required.
Reaction Conditions
The following representative conditions are drawn from literature precedents for chloroquinoline systems; they are provided as general guidance, not as product specifications.
Suzuki–Miyaura coupling (C-7):
Catalyst: Pd(dppf)Cl2·DCM (2–5 mol%) or Pd-PEPPSI-IPr (1–2 mol%)
Base: K3PO4 (2–3 equiv) or K2CO3
Solvent: 1,4-dioxane/H2O (3:1) or 2-MeTHF/H2O
Temp/time: 80–100 °C, 2–12 h; often 60–90% isolated yields depending on partner (literature ranges)
Solvent: MeCN or DMF; rt–60 °C, 2–18 h; protect if coupling catalysts are base-sensitive
Protection strategies:
Methylation (MeI/Me2SO4) or benzylation (BnBr) to mask OH prior to cross-coupling; deprotect by BBr3 (for Me) or hydrogenolysis (for Bn) (literature cautions apply).
Always monitor reactions by LC/MS or TLC; adjust for substrate electronics and sterics.
Safety & Handling
Item-specific GHS classification and hazard statements are not provided in the Product Data. Always consult the SDS for authoritative safety information.
GHS/Classification: Not specified for this item; refer to SDS.
Anticipated hazards (literature/generic for halogenated heteroaromatics): May cause irritation to skin, eyes, and respiratory tract. Avoid dust generation and inhalation.
Personal protective equipment (PPE):
Safety glasses or splash goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile)
Use in a chemical fume hood to control vapors/dust
Handling notes:
Avoid contact with strong oxidizers; phenolic compounds can be oxidized.
Avoid strong bases/acids when not intended, as they can drive tautomerization or O-deprotonation and promote side reactions.
Minimize exposure to moisture for coupling chemistry requiring anhydrous conditions.
First-aid overview (general):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse thoroughly with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Organic solid; treat as combustible. Use CO2, dry chemical, or foam. Thermal decomposition may release HCl/NOx (literature for chloro-heteroaromatics).
Waste: Dispose in accordance with institutional and local regulations; segregate halogenated organic waste streams where applicable.
Solvent Selection
This compound is a solid heteroaromatic building block, not a process solvent. Nonetheless, solvent choice is key for dissolution and reactivity.
Polarity class: Moderately polar, aromatic heterocycle; benefits from polar aprotic solvents for dissolution (literature).
Cross-coupling at C-7: dioxane/H2O, toluene, CPME, or Me-THF commonly used with Pd/Ni catalysts; add water if base requires biphasic/aqueous conditions.
O-alkylation/acylation at C-2 OH: polar aprotics (DMF, DMSO, MeCN) with bases such as K2CO3, Cs2CO3, or NaH.
Metalation/tautomer control: Ethers (THF) or toluene under strictly anhydrous conditions when using strong bases (e.g., LDA) to avoid side reactions.
MeCN/EtOH: greener profiles; may need warming or cosolvent.
CPME/2-MeTHF: greener ethers; good for Pd couplings; lower peroxide risk vs THF (still monitor).
Note: Optimize solvent considering base, temperature, and catalyst ligands to balance solubility and reaction rate.
Storage & Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store tightly capped in a dry, well-ventilated place away from strong oxidizers and strong acids/bases. Protect from prolonged light exposure to minimize photochemical degradation of heteroaromatics (general guidance).
Shipped in: Normal (per Product Data).
Reconstitution/preparation:
For stock solutions, dissolve in anhydrous DMSO, DMF, or MeCN to the desired concentration (e.g., 10–100 mM for screening or synthetic setups). Filter through a PTFE syringe filter if needed.
If aqueous work is required, use minimal DMSO/MeCN as cosolvent and add slowly to buffered aqueous media to avoid precipitation (research use only).
Freeze–thaw: For solution stocks, aliquot and store to minimize freeze–thaw cycles; solids generally tolerate ambient storage as specified.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet.
Always allow solid to equilibrate to room temperature in a closed container before opening to avoid moisture condensation. Verify concentration of stock solutions periodically by UV–Vis or quantitative NMR if used over extended periods (literature best practice).
Structure & Identity
A chloro-substituted quinolinol building block featuring a phenolic OH at C-2 and chlorine at C-7 on the quinoline skeleton. The scaffold offers an N-heteroaromatic ring fused to a benzene ring with a phenol/keto tautomerism at C-2.
Product name: 7-Chloro-2-hydroxyquinoline (research/lab use only)
CAS: 22614-72-8
CID (PubChem): 344137 (literature identifier)
Molecular formula: C9H6ClNO (literature)
Molecular weight: ~179.60 g/mol (literature)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features:
Quinoline core (benzannulated pyridine)
Substituents: 2-hydroxy (phenolic) group; 7-chloro on the benzene ring portion
Planar, conjugated π-system capable of π–π stacking and metal coordination via O/N donors (literature)
2D description: A bicyclic aromatic system with the ring nitrogen at position 1, hydroxy adjacent at position 2 on the pyridine ring, and chlorine para to the ring junction (position 7) on the fused benzene ring.
Synthetic Utility
Functional group set and reactivity (literature guidance):
Aryl chloride at C-7:
Entry point for C–C (Suzuki/Negishi/Stille), C–N (Buchwald–Hartwig), C–O/S (Ullmann-type or Pd-catalyzed) bond constructions.
Reactivity can be enhanced by electron-rich bulky phosphines (e.g., XPhos, SPhos) or NHC ligands for aryl chlorides.
Phenolic OH at C-2:
Readily deprotonated to phenoxide; O-alkylation/acylation affords protective or functional handles; Mitsunobu conditions can invert alcohol partners where relevant.
Can be transformed to triflate/mesylate (via transient protection/activation) enabling alternate cross-coupling manifolds from the oxygen site.
Tautomeric 2-quinolinone:
Enables N-acylation/alkylation chemistry; strategic control of tautomerism (base/solvent/temperature) allows orthogonal derivatization.
Directing/chelating effects:
The N/O motif can direct C–H activation on the ring system (e.g., ortho-arylation/alkylation under Pd/Ru catalysis) after suitable pre-coordination (literature).
Retrosynthetic value:
Serves as a convergent linchpin: arylation at C-7 installs diversity while the 2-OH offers a parallel vector for functionalization, enabling rapid matrix synthesis in SAR programs or materials libraries.
Target Specificity
Not an antibody, protein, or targeted biological reagent. No target specificity data apply.
Antigen/epitope/clone/isotype: Not applicable.
Species reactivity: Not applicable.
Refer to Reaction & Applications and Synthetic Utility for relevant chemical specificity (e.g., site-selective couplings).
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