This compound belongs to the class of organic compounds known as haloquinolines. These are compounds containing a quinoline moiety, which is substituted at one or more ring positions by n halogen atom.
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
165.140 g/mol
XLogP3
2.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Exact Mass
165.039 Da
Monoisotopic Mass
165.039 Da
Topological Polar Surface Area
12.900 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
163.000
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
Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are provided for this item. For synthetic use, follow literature procedures relevant to fluoroquinoline derivatization (see Reaction Conditions and Synthetic Utility tabs). Any protocol details (reaction scales, stoichiometries, or purification methods) should be optimized by the user for the intended transformation.
Biological Roles
This product is supplied for research use only. No biological activity or clinical utility is claimed for the material itself.
General context (literature):
Quinolines are prevalent motifs in natural products and bioactive small molecules. Fluorination is often used to modulate metabolic stability, lipophilicity, and electronic properties of heteroarenes.
The ring nitrogen can engage in H-bonding and cation–π interactions when protonated, which influences binding in enzyme and receptor active sites; however, specific target interactions for 5,8-difluoroquinoline are not established here.
Fluorine substituents can alter pKa and dipole, impacting passive permeability and protein binding in derived analogs; these are typically explored during SAR campaigns after further functionalization of the scaffold.
Because no biochemical/biological testing data are provided for this item, any roles should be considered theoretical and derived from the general behavior of quinoline frameworks. For experimental biological properties, consult primary literature on specific 5,8-difluoroquinoline derivatives rather than the parent scaffold.
Buffer Applications
Not typically applicable. 5,8-Difluoroquinoline is a hydrophobic heteroaromatic building block, not a buffering reagent. It does not constitute a defined acid/base pair with a suitable pKa/pH window for common laboratory buffers. For aqueous work, the compound may be protonated with strong acid to form water-soluble salts for extraction or crystallization, but this is not a buffering use.
For preparative work in water, consider using auxiliary buffers (e.g., phosphate, citrate) appropriate to your reaction or purification, while treating this compound as a non-buffered solute.
Green Alternatives
While 5,8-difluoroquinoline itself is a building block, greener choices relate to solvent selection and transformation strategy.
Strategy shifts (literature/general):
Prefer C–H functionalization (Ir/Rh-catalyzed borylation, Minisci-type functionalization on protonated quinoline) over halogen/defluoro installation-removal sequences to reduce halogenated waste.
Use catalytic nucleophilic substitution protocols (e.g., micellar catalysis, phase-transfer catalysis) to lower temperatures and minimize dipolar aprotic solvents.
Greener solvent options for common steps:
SNAr: Replace DMF/NMP/DMSO with Cyrene, propylene carbonate, sulfolane, or ethanol/water where feasible; consider 2-MeTHF or CPME for less polar cases.
Extractions/chromatography: Favor EtOAc, heptane, MeOH, and supercritical CO2 over chlorinated solvents when performance allows.
Comparison snapshot (general)
DMF/NMP/DMSO: Excellent for SNAr; reproductive toxicity or difficult workup. Tradeoff: performance vs EHS profile.
Cyrene/PC: Lower EHS footprint; may require higher temperature or longer time.
2-MeTHF/CPME/EtOAc: Good process solvents; limited polarity for very strong SNAr.
Waste and energy
Aim for telescoped sequences (e.g., in situ N-oxide formation/use) to reduce solvent swaps.
Employ base and solvent recycling in scale-up.
All recommendations are general sustainability guidance; confirm suitability for this specific substrate experimentally.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet.
General context (no therapeutic claims):
5,8-Difluoroquinoline can serve as a synthetic intermediate in the preparation of quinoline-based drug candidates, agrochemicals, and functional materials. Fluorination patterns at the 5 and 8 positions provide handles for diversification by SNAr or metal-catalyzed transformations, enabling rapid analog generation.
In medicinal chemistry workflows, such heteroaromatic building blocks are used for:
Fragment-based design and scaffold hopping around quinoline cores.
Installation of solubilizing side chains (e.g., via amination/alkoxylation) to tune ADME properties.
Generation of quinolinium salts to enhance crystallinity and facilitate purification of intermediates.
Regulatory note: This product is provided for research use only and is not intended for use in humans or diagnostics. No claims of GMP compliance or compendial listing are made unless explicitly stated on the CoA (not specified for this item).
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 (item): Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight (item): Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for 5,8-difluoroquinoline (reference only; not item specs)
Phase: Aromatic N-heteroaromatic typically encountered as a low-melting solid or high-boiling liquid; actual state depends on purity and temperature.
Volatility/boiling behavior: Quinoline boils near 237 °C (literature). Fluoro substitution often modestly alters bp; expect high-boiling behavior with low vapor pressure.
Basicity: The ring nitrogen is weakly basic; quinoline conjugate acid pKaH ≈ 4.9 (literature). Electron-withdrawing F substituents decrease basicity relative to quinoline, so salt formation in strong mineral acids is still straightforward.
Solubility profile: Expected to be sparingly soluble in water; soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, toluene, THF, acetonitrile) and in alcohols; readily soluble upon protonation in acidic aqueous media as the corresponding quinolinium salt.
Lipophilicity: Fluorination generally increases lipophilicity relative to the parent heteroarene; exact logP for this isomer not confirmed (literature value not verified).
Spectroscopic notes: Aromatic UV absorption with bands in the 200–350 nm range (typical of quinoline chromophores); 19F NMR shows two distinct aryl-F resonances; 1H NMR exhibits downfield ring protons adjacent to N and F.
For definitive numerical properties (mp, bp, density, refractive index, UV cutoff, water/peroxide content), consult the item’s CoA/Spec Sheet (not specified for this item).
Quality and Grades
Item grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance):
Research/technical grade is typically suitable for synthetic chemistry, library generation, and method development. Higher grades (e.g., >98% assay, HPLC-characterized) improve reproducibility in medicinal chemistry and SAR studies.
HPLC or LCMS traceable grade often indicates tight control of UV-absorbing impurities and provides full chromatographic profile.
Impurities and profile considerations (general):
Potential related substances include mono-fluoroquinoline isomers, unfluorinated quinoline, and over-oxidized materials (e.g., quinoline N-oxide). Residual halogenated solvents may be relevant depending on synthesis route.
For electrophilic aromatic substitution or SNAr chemistry, trace metal content is usually less critical than for cross-coupling; however, if used in metal-catalyzed steps (e.g., borylation), low residual sulfur/phosphorus and halide salts can be beneficial.
Documentation: Request the batch-specific Certificate of Analysis for assay, identification (NMR/HRMS/GC/LC), residual solvents, and moisture data. Any values not listed here are not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Reaction and Applications
Role in synthesis (general): 5,8-Difluoroquinoline is a functionalized quinoline scaffold valuable for preparing 5- or 8-substituted quinolines via nucleophilic aromatic substitution (SNAr) at aryl–F positions and for site-selective derivatization of the quinoline core.
SNAr at aryl–F: Electron-withdrawing ring N activates the benzene ring toward SNAr. Strong nucleophiles (primary/secondary amines, alkoxides, thiolates) can displace F at activated positions under heating in DMSO/DMF/NMP with Cs2CO3/K2CO3 or NaH. Regioselectivity depends on position (5 vs 8) and nucleophile hardness.
Directed metalation: The quinoline N (and sometimes F as an ortho/para director) enables deprotonation at specific positions (e.g., C-2/C-4) using s-BuLi/LiTMP at low temperature, allowing subsequent electrophile trapping (formylation, borylation, silylation).
N-oxidation and rearrangements: Oxidation to the N-oxide (mCPBA) followed by electrophilic substitution or the Boekelheide rearrangement can provide access to oxygenated derivatives; N→O strategies can also modulate reactivity for SEAr.
C–H activation: Ir/Rh-catalyzed borylation or arylation of quinolines is known; fluorine substituents can influence directing/selectivity. Subsequent Suzuki couplings diversify the scaffold.
Lithiation–halogen exchange or halodefluorination under specialized conditions can convert C–F to C–Cl/C–Br for more routine cross-coupling.
Application domains (no clinical claims):
Discovery chemistry and SAR around quinoline pharmacophores.
Fluorinated heteroarene fragments in materials and ligand development.
Note: The above are literature/general uses of fluoroquinolines; verify conditions for this specific isomer experimentally.
Reaction Conditions
General literature guidance for fluoroquinoline transformations (example ranges; verify for this isomer experimentally):
Base: Cs2CO3, K2CO3 (amines/phenoxides) or NaH/KOtBu (alkoxides/thiolates).
Solvent: DMSO, DMF, NMP, or sulfolane; in some cases, EtOH or 2-MeTHF with phase-transfer catalyst.
Temperature: 80–160 °C (oil bath/sealed tube), 4–24 h.
Notes: Regioselectivity between C-5 and C-8 can depend on nucleophile hardness and reaction temperature; analytical monitoring by 19F NMR is recommended.
Directed ortho-metalation (DoM)
Base: s-BuLi or LiTMP, −78 to −30 °C in dry THF/Et2O under N2/Ar.
Electrophiles: CO2 (carboxylation), DMF (formylation), B(OMe)3 (borylation), Me3SiCl (silylation).
Quench: NH4Cl or MeOH at low temperature; warm to rt before aqueous workup.
N-oxidation and subsequent transformations
Oxidant: mCPBA or peracetic acid in DCM/CHCl3 at 0–25 °C.
Follow-up: Boekelheide rearrangement with acylation reagents; subsequent reduction of N-oxide (PCl3, Zn/AcOH) if needed.
C–H borylation
Catalyst: [Ir(dtbpy)(COD)]BF4 (or related), B2pin2, 80–120 °C, dioxane/THF.
Downstream: Suzuki coupling (Pd catalysts) in 1,4-dioxane/H2O with K2CO3 or Cs2CO3, 60–100 °C.
These conditions are representative from literature for quinoline/fluoroquinoline systems and are not item-specific specifications.
Safety and Handling
Item-specific hazard information
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General safety guidance for fluorinated quinolines (literature/analog-based; defer to SDS)
Likely hazards: May cause skin/eye irritation and respiratory tract irritation. Aromatic amines/aza-arenes can have moderate acute toxicity; avoid ingestion and inhalation of dust/vapors.
Personal protective equipment (PPE): Use lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a functioning chemical fume hood.
Handling: Avoid breathing dust or vapors. Prevent contact with skin and eyes. Do not use near ignition sources; although high-boiling, organic vapors can be combustible.
Incompatibilities: Strong oxidizing agents (risk of exothermic reaction), strong acids/bases (may lead to salt formation or decomposition), and reactive alkali metals. Avoid halogenation/oxidation conditions unless controlled.
First aid measures (overview; consult SDS):
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; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/accidental release: Absorb with inert material (e.g., vermiculite), collect in chemical waste. Ventilate area.
Waste disposal: Dispose of as halogenated organic waste per institutional and local regulations.
Always consult the product-specific SDS for authoritative hazard, toxicological, and regulatory information (not specified for this item).
Solvent Selection
Applicability: 5,8-Difluoroquinoline is a hydrophobic, weakly basic, aromatic heterocycle. Solvent choice is typically driven by its use as a reactant/intermediate rather than as a solvent itself.
Polarity/miscibility (general expectations):
Sparingly soluble in water as the free base; forms water-soluble salts under acidic conditions (e.g., HCl, H2SO4) for workup or purification.
Good solubility in common organic solvents: dichloromethane, chloroform, ethyl acetate, toluene, THF, acetonitrile, and alcohols (MeOH/EtOH) depending on temperature.
Typical solvent choices by application:
SNAr with amines/phenoxides: polar aprotic solvents (DMSO, DMF, NMP) to enhance nucleophilicity; elevated temperature.
Metalation/functionalization (e.g., directed ortho-metalation): ethereal solvents (THF, MTBE) at low temperature under inert atmosphere.
Cross-coupling after C–F activation (specialized catalysts): high-boiling, polar solvents (DMAc, dioxane) can be advantageous.
Salt formation/crystallization: alcohols/ethers for antisolvent precipitation after acidification.
Practical selection tips:
Start with DCM or EtOAc for extraction and normal-phase chromatography.
If basic impurities co-elute, switch to buffered mobile phases or use reversed-phase LC with MeCN/H2O + acid modifier for analytical control.
For scale-up, favor greener solvents when feasible (EtOAc, 2-MeTHF, CPME) while confirming solubility and reaction rates.
Storage and Reconstitution
Item-specific storage and shipping
Storage Conditions: Room temperature (as provided in Product Data).
Shipped In: Normal (ambient) conditions (as provided in Product Data).
General handling and stability (not item-specific specs)
Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged light exposure to minimize degradation or discoloration typical of aza-arenes.
Under inert gas (N2/Ar) is advisable for long-term storage, especially after opening, to limit oxidative byproducts (e.g., trace N-oxide formation).
Reconstitution/solubility guidance (general)
Solubility: Typically soluble in common organic solvents (DCM, CHCl3, EtOAc, MeCN, THF, toluene) and in alcohols; sparingly soluble in water as free base.
Preparing stock solutions: For analytical or screening use, prepare 10–100 mM stocks in DMSO or MeCN; filter if particulates are present. For aqueous applications, dissolve in minimal organic solvent or convert to a protonated salt (e.g., HCl) to enhance water solubility.
Freeze–thaw: If stored in solution, aliquot to avoid repeated freeze–thaw cycles that can introduce moisture/oxygen.
For any unspecified parameters (e.g., exact solubility, stability limits), consult the batch CoA/Spec Sheet. Research use only.
Structure and Identity
Brief description: 5,8-Difluoroquinoline is a fluorinated quinoline (benzopyridine) bearing fluorine atoms at the 5- and 8-positions of the fused aromatic system.
Item identifiers (Product Data)
CAS: 16650-32-1
CID: 155433
InChIKey (as provided): 326196
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identifiers (for reference; not item specifications)
Molecular formula (literature): C9H5F2N
Molecular weight (literature): ~165.14 g/mol
Structural features (general/literature)
Core scaffold: quinoline (a benzene ring fused to a pyridine ring; one endocyclic ring nitrogen at position 1).
Substitution pattern: fluorine atoms on the benzene portion of quinoline at C-5 and C-8 (peri to the ring junction and para/meta relative to the ring N depending on numbering conventions).
Functional groups: two aryl–F bonds; one ring sp2 nitrogen (weakly basic).
2D description in words: A bicyclic, planar, polyaromatic system consisting of a pyridine ring fused to a benzene ring; the benzene ring bears F substituents at positions 5 and 8 relative to the ring nitrogen.
Stereochemistry: None (achiral, fully aromatic).
Synthetic Utility
Key reactivity elements (general/literature):
Electrophilic aryl C–F bonds at C-5 and C-8 can undergo SNAr with hard nucleophiles under forcing conditions, enabled by the ring nitrogen’s electron-withdrawing influence on the benzene ring.
The quinoline nitrogen directs metalation at adjacent positions (e.g., C-2/C-4) allowing regioselective deprotonation and subsequent trapping with electrophiles (formylation, silylation, borylation). Fluorine substituents further bias regioselectivity by deactivating/activating positions and serving as potential leaving groups.
N-oxide strategies temporarily increase ring activation, facilitating electrophilic aromatic substitution and rearrangements (Boekelheide), giving access to oxygenated or rearranged derivatives, which can then be reduced back to the quinoline.
5,8-Difluoro substitution pattern offers orthogonal handles: one F may be retained for electronic tuning while the other is displaced to introduce functional groups, enabling divergent synthesis of 5- or 8-substituted libraries from a single starting point.
Analytical considerations:
19F NMR provides a sensitive handle to track substitution at C-5/C-8. LC–MS with ESI readily detects the [M+H]+ at m/z ~166 (literature), aiding reaction monitoring.
Target Specificity
Not applicable. This product is a small-molecule heteroaromatic building block, not a biological targeting reagent (e.g., antibody, aptamer, inhibitor with defined target). No antigen/epitope or species reactivity applies.
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