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
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
181.140 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Exact Mass
181.034 Da
Monoisotopic Mass
181.034 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
254.000
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
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Recensioni
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Application Protocols
No item-specific tested biological application protocols are provided. As a synthetic building block, typical laboratory uses include:
Solution preparation (general):
Prepare 10–100 mM stock solutions in dry DMSO. Warm gently and sonicate if needed.
For screening or assays, dilute stocks into buffer to a final DMSO content typically ≤1–2% v/v, checking for precipitation.
Synthetic setup (general):
For SNAr: Charge substrate, base, nucleophile, and anhydrous polar aprotic solvent under inert atmosphere; heat to target temperature and monitor by LC/MS.
For O-alkylation: Use carbonate base in acetone/MeCN; add alkyl halide slowly to control exotherm; monitor regioselectivity.
For any specific application, validate and optimize conditions empirically. Consult the SDS before handling.
Biological Roles
This substance is a synthetic difluorinated quinolinol used for research and synthesis. There are no known endogenous biological roles for 5,7-difluoro-4-hydroxyquinoline itself.
Quinoline motif (literature context): The quinoline scaffold is common in bioactive small molecules, coordinating to metal ions and engaging in π–π and cation–π interactions with biomolecular targets. Incorporation of fluorine often modulates lipophilicity, membrane permeability, and metabolic stability.
Tautomerism and binding: The 4-hydroxy/4-quinolinone tautomerism provides hydrogen-bond donor/acceptor capabilities that can be leveraged in fragment-based design or structure–activity relationship (SAR) studies.
Probe development: The heteroaromatic nitrogen can participate in protonation-dependent binding and pH-sensitive behaviors, useful in designing pH-responsive probes or ligands for biochemical assays (research use only).
Important: The above are general, literature-based considerations for quinoline chemistry and do not imply any specific biological activity or suitability for clinical/diagnostic use. This product is provided strictly for research use only as stated by the manufacturer.
Buffer Applications
Not typically applicable. 5,7-Difluoro-4-hydroxyquinoline is a hydrophobic heteroaromatic building block and is not used as a buffering agent or pH stabilizer.
If dissolution in aqueous systems is needed for assays, prepare concentrated stock solutions in DMSO and dilute into buffered media (e.g., phosphate or HEPES), keeping final organic content low to avoid precipitation.
Adjusting pH to mildly basic values can transiently increase solubility via phenolate formation, but this also changes chemical speciation and reactivity; confirm compatibility with your assay.
Green Alternatives
Green chemistry considerations focus on solvent choice and activation strategies that minimize waste and hazard while maintaining reactivity for SNAr and O-alkylation.
Solvent substitution (literature guidance):
Replace high-boiling, difficult-to-remove solvents (DMF, NMP) with MeCN, 2-MeTHF, or CPME when feasible.
For SNAr, propylene carbonate and sulfolane can offer greener polarity with higher flash points; evaluate removal and potential hydrolytic effects.
Comparison (general):
| Context | Conventional | Greener alternative | Trade-offs |
|---|---|---|---|
| SNAr with amines | DMF, DMSO | MeCN, propylene carbonate, 2-MeTHF | May require higher temp or longer time |
| O-alkylation | DMF/acetone | 2-MeTHF/MeCN | Base solubility can limit scope |
| Workup | DCM | EtOAc, IPA | Polarity mismatch can affect recovery |
Catalysis: Favor microwave heating or flow chemistry to reduce time/energy. For C–F activation, consider nickel catalysts or photoredox to avoid stoichiometric metal waste (literature), recognizing that enabling conditions may be substrate-specific.
Waste minimization: Use solid-supported bases (e.g., polymer-bound) to streamline workup; adopt phase-switching crystallizations to avoid chromatographic silica waste.
Safety/health: Avoid DMF/NMP where worker exposure limits are constrained; ensure closed systems if used. Choose low-toxicity, biodegradable solvents where performance allows.
Note: Validate greener options at small scale; electronic effects from the quinoline N and difluoro pattern can shift optimal conditions.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item. It is provided for research and synthetic use only.
Role (general): Quinoline derivatives are prevalent intermediates in the synthesis of small-molecule drug candidates. The difluoro pattern (5,7-F) offers a handle for late-stage diversification via SNAr to tune physicochemical properties during lead optimization.
Formulation context: Not typically used as a formulation excipient. If used in discovery biology, compound is usually handled as DMSO stock solutions for in vitro screening (research use only).
Regulatory: No USP/EP monograph is known for this specific difluorinated quinolinol (literature context). For any development work, comprehensive impurity profiling and solid-state characterization (polymorph, solvate) would be required at later stages.
Note: No therapeutic or clinical claims are made or implied for this product.
Physical Properties
Item-specific physicochemical specifications are not provided in the catalog entry.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula / MW: C9H5F2NO; ~181.14 g/mol (literature, computed).
Melting point / Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density / Refractive index: Not applicable/unknown for a solid; item-specific data not provided.
Solubility (qualitative, literature):
Likely sparingly soluble in water due to aromaticity and fluorination; solubility may increase under basic conditions via phenolate formation.
Readily soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP). Solubility in alcohols, acetone, and chlorinated solvents is expected to be moderate; heat and sonication often assist dissolution.
pKa (qualitative, literature):
Phenolic OH of 4-hydroxyquinolines typically pKa ~9–10; tautomerization to 4-quinolinone influences acidity/basicity.
The ring pyridine N has basicity in the weak base range (conjugate acid pKa typically ~4–5 for quinolines).
LogP (expectation, literature): Aromatic difluorination increases lipophilicity versus non-fluorinated analogs; exact value not specified.
Practical notes (general):
Warm solvent (40–60 °C), brief sonication, or mild base (for phenolate generation) can aid dissolution in method development. For analytical work, prepare stock solutions in dry DMSO or DMF and dilute into the working medium to minimize precipitation.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
In the absence of an explicit grade, users should verify that the supplied purity, residual solvents, and elemental analysis meet the needs of their application (e.g., medicinal chemistry vs. materials R&D).
Typical grade descriptors (general guidance):
Research grade: Suitable for synthetic and discovery workflows; may include trace impurities not controlled at analytical reagent levels.
Analytical/AR grade: Tight controls on assay and common impurities; often accompanied by UV cut-off data for spectroscopic use.
HPLC grade (for solvents): Not applicable to this solid, but the concept involves low UV absorbance and tight nonvolatile residue control.
Stabilizers/Inhibitors: None specified for this item. 4-hydroxyquinoline systems are generally stable without added stabilizers; protect from prolonged light and heat.
Batch documentation: Request and review the Certificate of Analysis (CoA) for lot-specific details: assay methodology (e.g., qNMR, HPLC), water content (Karl Fischer), residual metals/halides (if relevant), and chromatographic purity.
Use recommendations: For structure-activity exploration and library synthesis, consider a short incoming QC (HPLC, HRMS, optional NMR) before campaign-scale use, especially when developing sensitive SNAr or alkylation transformations where impurities can catalyze side reactions.
Reaction and Applications
5,7-Difluoro-4-hydroxyquinoline is a versatile heteroaromatic building block enabling orthogonal transformations on the C–F bonds, the 4-hydroxy/4-quinolinone functionality, and the ring nitrogen environment.
SNAr diversification (literature):
The 5- and 7-positions are activated toward nucleophilic aromatic substitution by the adjacent ring nitrogen and the electron-withdrawing effect of fluorine. Amines, alkoxides, and thiolates can displace F under elevated temperatures in polar aprotic solvents (DMF, DMSO, NMP). Cesium carbonate or sodium tert-butoxide are common bases; the 5-position may be more reactive depending on substituent patterns.
O- vs N-functionalization:
The 4-hydroxy tautomer (↔ 4-quinolinone) allows O-alkylation/acylation to generate 4-alkoxy or 4-acyloxy derivatives. Competing transformations at the ring nitrogen can occur under strongly basic or Mitsunobu-type conditions—optimize base, solvent, and temperature to control selectivity.
Cross-coupling strategies:
Direct Pd-catalyzed coupling of aryl C–F is challenging; strategies include prior borylation or halogen exchange (e.g., convert C–F to C–B or C–Br/I) or nickel-mediated activation under strong conditions (literature). Alternatively, functionalize via directed metalation adjacent to the ring N followed by electrophile quench.
Heteroaryl N-oxide/N-oxide rearrangements: Oxidation to the quinoline N-oxide can tune electronics for subsequent substitution, then reductive removal restores the parent N.
Applications: Synthesis of diversified quinoline libraries, ligand frameworks, and materials motifs where fluorine content modulates lipophilicity, metabolic stability, or photophysical properties (research context).
Practical tip: Thorough drying of solvents and exclusion of water increases SNAr efficiency; microwave heating can substantially reduce reaction times.
Reaction Conditions
General literature guidance for analogous quinoline systems; optimize for your substrate and scale.
Base: Cs2CO3, K2CO3, NaOtBu (0.5–2.0 equiv depending on nucleophile strength).
Temperature/Time: 60–140 °C; 1–24 h. Microwave can reduce time to 10–60 min.
Notes: Control water content (<500 ppm desirable) to favor substitution; monitor regioselectivity by LC/MS.
O-Alkylation (forming 4-alkoxyquinolines):
Electrophiles: Alkyl halides/sulfates.
Base: K2CO3, Cs2CO3; occasionally Ag2O for benzylic halides.
Solvents: Acetone, MeCN, DMF.
Temperature: RT–80 °C; 2–18 h.
Notes: Competing N-alkylation on the ring nitrogen can occur; lower temperatures and weaker bases favor O-alkylation.
Acylation (forming esters or 4-quinolinone derivatives):
Reagents: Acyl chlorides/anhydrides, EDC/HATU for carbamate/ester formation.
Base: Pyridine, DIPEA.
Solvents: DCM, THF, DMF; 0–25 °C.
N-oxide route:
Oxidation: mCPBA or peracids in DCM/MeCN (0–25 °C).
Deoxygenation: PCl3, Zn/AcOH, or P(III) reagents.
Cross-coupling (after pre-activation):
Prepare aryl boronates or halides, then Suzuki (Pd(0), base, aqueous biphasic), Buchwald–Hartwig (Pd, bulky ligands), or Sonogashira (Pd/Cu).
Yields: Highly substrate- and condition-dependent; literature reports for analogous SNAr often range 50–90% under optimized conditions. Always confirm on small scale before scale-up.
Safety and Handling
Authoritative safety information must be taken from the product SDS. The following are general handling considerations for halogenated heteroaromatics.
GHS/CLP classification: Not specified for this item; consult the SDS for signal word, hazard statements, and pictograms.
Primary hazards (general): May cause skin/eye irritation and respiratory irritation as a fine organic powder. Avoid dust formation and inhalation. Combustible as with most organic solids.
Incompatibilities: Strong oxidizers; strong bases/acids under forcing conditions may promote decomposition or substitution. Fluoroaromatics are generally stable but can undergo SNAr with strong nucleophiles at elevated temperature.
Personal protective equipment (typical lab): Laboratory coat, safety glasses or chemical splash goggles, and appropriate gloves (e.g., nitrile). Use in a fume hood to control dust and vapors from heated solutions.
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; remove contact lenses if present and easy to do; continue rinsing.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: Use CO2, dry chemical, or foam. Combustion may release toxic fumes (e.g., HF in trace from fluorinated aromatics and NOx). Firefighters should wear self-contained breathing apparatus.
Spill response: Avoid raising dust; collect mechanically or with inert absorbent; dispose of according to local regulations.
Always refer to the SDS for definitive classification and response measures.
Solvent Selection
As a halogenated heteroaromatic phenol (tautomeric 4-quinolinone), this compound exhibits modest polarity and poor aqueous solubility.
Polarity class (general): Moderately polar aromatic heterocycle; capable of H-bonding (donor/acceptor via OH/quinolinone tautomer; ring N = acceptor).
Preferred solvents (literature/practice):
Stock solutions: DMSO, DMF, or NMP for high-concentration solutions.
Workup/processing: EtOAc, MeCN, acetone, THF, dichloromethane as diluents; solubility may require warming.
Crystallization: Aromatic solvents (toluene, chlorobenzene) or EtOAc/hexane mixtures depending on substitution and salt form.
Aqueous systems: Water solubility is limited; basic aqueous media can increase solubility by forming the phenolate, but may alter reactivity.
Selection guidance:
For SNAr with amines/thiols, use polar aprotic solvents (DMF, DMSO) to enhance nucleophilicity; ensure low water content.
For O-alkylation or N-oxide/N-alkyl chemistry, choose solvents that balance base solubility and substrate stability (acetone, MeCN, or DMF) and monitor for competing N- vs O-alkylation.
For analytical HPLC, dissolve in DMSO or MeCN, then dilute into aqueous mobile phase containing a small % organic and modifier (e.g., 0.1% formic acid or ammonium formate) as needed.
Comparison (general):
DMSO/DMF offer superior solvating power vs. MeCN or acetone but complicate removal; choose based on downstream isolation needs.
Storage and Reconstitution
Storage Conditions (catalog): Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General stability: Quinoline derivatives with phenolic functionality are generally stable at ambient temperature. Protect from excess heat, moisture, and prolonged light exposure to maintain assay integrity.
Container: Store tightly closed in an amber glass vial with desiccant if possible. Minimize headspace for long-term storage.
Reconstitution/Dissolution (general):
Prepare stock solutions in anhydrous DMSO or DMF. Typical concentrations: 10–100 mM.
To aid dissolution, warm to 40–60 °C and sonicate briefly. Filter through 0.2 µm PTFE if particulate persists.
For aqueous work, dilute the organic stock into buffered media with mixing; monitor for precipitation and adjust pH if appropriate for your assay.
Freeze–thaw: For solutions, aliquot to avoid repeated freeze–thaw. Store DMSO solutions at –20 °C for extended periods; allow to equilibrate to room temperature before opening to prevent moisture ingress.
Shelf life: Not specified for this item; monitor by HPLC/LC–MS periodically for critical uses.
Always consult the CoA and SDS for lot-specific recommendations and stability information.
Structure and Identity
A difluorinated quinolinol scaffold useful as a heteroaromatic building block and SNAr handle.
Product Name (SKU): 5,7-Difluoro-4-hydroxyquinoline (D479609)
CAS: 874804-43-0
PubChem CID (catalog): 43531984 (literature)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: C9H5F2NO (literature, derived from name)
Molecular Weight: ~181.14 g/mol (literature, computed from formula)
Structural features (descriptive):
Core ring system: Quinoline (benzannulated pyridine) with a heteroaromatic ring nitrogen at position 1.
Substituents: Fluorine atoms at the 5- and 7-positions on the benzenoid ring; a hydroxy group at the 4-position. The 4-hydroxy/4-oxo system exhibits tautomerism (4-hydroxyquinoline ↔ 4-quinolinone), with the keto (quinolinone) form often favored in polar media (literature).
Functional groups: Aromatic C–F bonds (strongly deactivating/ortho-para directing within the benzenoid ring), phenolic OH (acidic), and a ring pyridine-type nitrogen (basic/ligating).
2D description: A fused bicyclic aromatic system with the pyridine ring fused to a benzene ring; the OH at C-4 is para to the ring junction and flanked by fluorines at C-5 and C-7 on the benzenoid portion; N is at the alpha position of the pyridine ring.
Notes: Identity parameters not listed above as item-specific are provided as literature descriptors only and should be verified against the product CoA for regulated or critical applications.
Synthetic Utility
This scaffold enables orthogonal reactivity, making it a valuable node in retrosynthetic planning for quinoline-containing libraries.
Electrophilic handles: Two activated aryl C–F bonds at C-5 and C-7 enable SNAr with O-, N-, and S-nucleophiles. Electronic bias from the ring nitrogen and the 4-oxo/4-OH tautomer can influence positional selectivity.
Nucleophilic center: The phenolic oxygen at C-4 (tautomeric with a 4-quinolinone) can be alkylated or acylated to access ethers/esters; careful base choice can suppress undesired N-alkylation (on the ring nitrogen) or overreaction.
Ring nitrogen manipulations: Oxidation to quinoline N-oxide can activate the ring toward substitution at otherwise inert positions, followed by deoxygenation to restore the parent N.
Cross-coupling routes: Although direct Pd-catalyzed activation of C–F is challenging, halogen exchange (e.g., via lithiation then quench with electrophilic halogen) or borylation (e.g., Ni-catalyzed) can render positions 5/7 compatible with Suzuki, Buchwald–Hartwig, or Sonogashira couplings (literature).
Directed metalation: The ring nitrogen can direct ortho-lithiation under strong bases/low temperatures, offering access to otherwise inaccessible substitution patterns, followed by electrophile trapping.
Protecting group strategy: Temporary O-protection (e.g., silyl ethers, carbonate) can be used to control selectivity during multi-step sequences.
These complementary modes allow rapid assembly of diverse analogs for SAR, ligand design, and materials exploration.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological probe with defined target specificity.
No antigen, epitope, clone, or isotype information applies.
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