GRADE & PURITYReagent Grade?General reagent-grade purity suitable for most laboratory work. Use as a dependable default when no specific higher grade is required.
This compound belongs to the class of organic compounds known as chloroquinolines. These are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
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.
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Application Protocols
No assay or immunoapplication protocols are provided for this small-molecule building block in the Product Data.
General laboratory use
For solution preparation, dissolve the compound in an appropriate dry organic solvent (e.g., DMSO, DMF, THF, toluene, or DCM) to the desired concentration for reaction setups or stock solutions.
For combinatorial synthesis, plan orthogonal functionalization (C4 vs C6) and include appropriate controls (blank reactions, catalyst-only controls) in screening plates.
Analytics (general guidance)
Monitor reactions by TLC (UV-active quinoline chromophore), HPLC/UPLC with UV detection (254–300 nm), and LC–MS for mass confirmation.
Refer to the SDS and CoA for any handling nuances before developing internal SOPs.
Biological Roles
Item-specific biological data are not provided. The following comments describe general properties of the quinoline scaffold in biochemical research; they are not safety or clinical claims.
Quinoline as a research motif (general/literature)
Quinolines are prevalent in research ligands for enzymes, GPCRs, kinases, and as chromophores. Substitution around the ring (including at C4 and C6) modulates electronics, basicity, and lipophilicity, influencing binding in SAR programs.
Chloro substituents serve as synthetic handles rather than bioactive groups per se; they can be diversified to amino, aryl, alkoxy, and thioether substituents to probe biological targets.
The ring nitrogen can act as a weak base and metal ligand, enabling coordination to metal centers in bioinorganic models and probes.
Physicochemical considerations
The hydrophobic, heteroaromatic character contributes to membrane permeability in small-molecule probe design. The 8-methyl group can act as a point for metabolic oxidation (to alcohol/aldehyde/acid) in metabolism studies of derived analogs.
No specific biological role is assigned to 4,6-dichloro-8-methylquinoline itself in the Product Data. For research use only; not for diagnostic, therapeutic, or veterinary applications.
Buffer Applications
This compound is a hydrophobic heteroaromatic building block and is not typically used to prepare aqueous buffers or as a buffering agent.
Not typically applicable: It lacks the requisite acid/base pKa pair and aqueous solubility profile for conventional buffer systems.
Practical note: When handling in aqueous workflows (e.g., bioconjugation of derivatives), solubilize in a miscible organic cosolvent (DMSO, DMF) before dilution, and verify compatibility of the organic content with your biological system.
Green Alternatives
While 4,6-dichloro-8-methylquinoline is a specific heteroaromatic building block (not readily replaced by a “green” analogue), greener choices can be implemented in how it is transformed.
Greener coupling practices (literature/general)
Solvent substitution: Replace dioxane/DMF with 2-MeTHF, CPME, or water/biobased surfactant systems (micellar catalysis) when feasible.
Catalyst systems: Use highly active ligands (e.g., XPhos/SPhos/BrettPhos) to lower catalyst loading and temperature; explore nickel catalysis for aryl chlorides.
Bases: Favor carbonate/phosphate bases over strong/hazardous bases when compatible.
Chloride vs bromide/iodide
Aryl chlorides are more abundant and often greener and cheaper than bromides/iodides, but require more active catalysts. Using the chloride substrate avoids halogen-upgrading steps and reduces halogenated waste.
Workup/waste minimization
Apply telescoped sequences (e.g., sequential C4 then C6 functionalization in one pot) to limit solvent use.
Use solvent recovery (distillation) and phase-optimized extractions to minimize chlorinated solvent consumption.
Comparison snapshot (general guidance)
Conventional: DMF or dioxane, Pd(PPh3)4, aryl boronic acid, 100–110 °C.
Greener: 2-MeTHF/H2O or aqueous micelles, modern Pd or Ni catalysts with biaryl phosphines, 50–80 °C, reduced catalyst loading.
These are process choices; the heteroaromatic core itself typically has no direct “green” substitute for structure-specific research applications.
Pharmaceutical Uses
No pharmacopeial or excipient role is specified for this item. The following reflects general practice for heteroaromatic building blocks in pharmaceutical R&D (not clinical claims):
Role in drug discovery (general)
Functions as an intermediate for synthesizing quinoline-containing lead compounds and SAR libraries via cross-coupling or SNAr diversification at C4/C6, with optional modification at the 8-methyl position.
Useful for generating structure–activity relationships where the quinoline core acts as a heteroaromatic pharmacophore or metal-binding motif.
Formulation/excipient status
Not used as an excipient; no compendial (USP/EP/JP) status indicated in the Product Data.
Manufacturing considerations
Downstream purification of derived APIs often removes residual starting materials like this building block to trace levels; analytical methods include HPLC/LC–MS with UV detection leveraging the quinoline chromophore.
For research use only; not for human or veterinary use.
Physical Properties
Item-specific specifications for this product (appearance, MP/BP, density, UV cutoff, elemental limits, residuals) are not provided in the Product Data. Where applicable, consult the CoA/Spec Sheet.
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density/refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Literature/structure-based expectations (general guidance, not specifications)
Physical state: Quinoline halo-derivatives of this size are typically crystalline solids at ambient temperature.
Basicity: Quinoline conjugate acid pKaH ~4.9 (literature); two chloro substituents may slightly lower basicity relative to quinoline due to −I effects.
Polarity/partitioning: Aromatic chloro-heterocycles are generally hydrophobic with low water solubility; logP expected to be moderately high relative to quinoline (qualitative).
Solubility profile: Commonly soluble in chlorinated solvents (e.g., DCM/CHCl3), aromatics (toluene), ethers (THF), and polar aprotics (DMF/DMSO/MeCN); sparingly soluble in water (qualitative, literature trend for substituted quinolines).
Thermochemical/optical (literature trends)
Aromatic UV absorption: Quinoline chromophore typically shows strong absorption in the 230–330 nm region; substitution perturbs λmax and intensity (qualitative note only).
Always verify exact physical data for the specific lot via the CoA before process design or scale-up.
Quality and Grades
Item-specific grade (from Product Data)
Reagent Grade: Suitable for general laboratory synthesis and research applications. Reagent Grade typically signifies compliance with commonly accepted purity for preparative work but is not necessarily optimized for spectroscopic or chromatographic baselines (e.g., not necessarily HPLC or LC–MS grade).
What Reagent Grade implies (general guidance)
Purity is typically adequate for synthetic transformations, SAR library preparation, and method development.
Trace impurities, moisture content, or UV-absorbing background are not tightly controlled as in “HPLC grade” or “Ultra Dry” specifications.
When to consider higher grades
For highly sensitive catalysis, kinetics, photophysics, or trace analysis, verify impurity profiles and consider additional purification in-house (recrystallization, chromatography) or request higher-grade material if available.
Stabilizers/additives
None specified for this item; refer to CoA/Spec Sheet for any lot-specific notes.
Documentation
For quantitative specifications (assay, residual solvents, elemental analysis), consult the CoA/Spec Sheet for this SKU. Lot-specific testing may include NMR, HPLC, GC, MS, or elemental analysis as applicable.
Reaction and Applications
4,6-Dichloro-8-methylquinoline is a versatile bifunctional aryl chloride on a quinoline scaffold. Its two C–Cl bonds and benzylic 8-methyl group enable complementary synthetic strategies.
Cross-coupling platform (literature/general)
Suzuki–Miyaura: Sequential arylation/alkenylation at C4/C6 using Pd catalysts. Chlorides are less reactive than bromides/iodides; use ligand-activated systems (e.g., XPhos, SPhos, RuPhos, BrettPhos) to promote oxidative addition.
Buchwald–Hartwig amination: Installation of anilines or alkylamines to furnish aminoquinolines; choose conditions to differentiate C4 vs C6 reactivity (ligand, base, temperature) for regioselective mono- vs difunctionalization.
Kumada/Negishi/Stille: Feasible with appropriate organometallic partners and catalyst systems.
Nucleophilic aromatic substitution (SNAr)
Quinoline C4–Cl is typically activated by the ring nitrogen; under strong base/heat, amines, alkoxides, thiolates can displace chloride. C6–Cl is also susceptible albeit often less activated; stepwise, chemoselective SNAr is possible.
Benzylic functionalization at C8-methyl
Oxidation: SeO2 (allylic/benzylic), MnO2 or chromium(VI)-free protocols to aldehyde/acid derivatives.
C–H activation: Directed benzylic C–H oxidation or amination methods reported for methyl quinolines.
Lithiation: Directed deprotonation at the benzylic position with strong bases (e.g., LDA/TMEDA) enables electrophile trapping (formylation, alkylation).
Applications
Assembly of N-heteroaromatic libraries, ligands for coordination chemistry, dye/optical materials precursors, and intermediates in agrochemical or materials research. The dual-chloro motif allows orthogonal diversification for rapid SAR.
Note: No medical or clinical claims; for research use only.
Reaction Conditions
The following are literature-style, general conditions for aryl chloride functionalization on quinoline scaffolds; verify and optimize for your substrate and scale. Values are guidance, not item specifications.
Suzuki–Miyaura coupling (Ar–Cl at C4 or C6)
Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with XPhos/SPhos (2–4 mol%) or Pd-PEPPSI-type precatalysts.
Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv).
Solvent: 1,4-dioxane/H2O, THF/H2O, 2-MeTHF/H2O; 70–110 °C, 4–16 h.
Notes: C4–Cl often couples faster; temperature/ligand can tune C4 vs C6 selectivity. Aqueous micellar media can lower temperature.
Buchwald–Hartwig amination
Catalyst/ligand: Pd(OAc)2 (1–2 mol%) with BrettPhos/RuPhos or Pd–XPhos precatalysts.
Base: NaOtBu or K3PO4; solvent toluene, tAmOH, or dioxane; 80–110 °C.
Notes: For challenging amines or C6–Cl, increase ligand donor strength and temperature.
SNAr with amines/alkoxides
Reagents: Amine or alkoxide (2–5 equiv), base (NaH, KOtBu, Cs2CO3), polar aprotic solvent (DMF, DMSO, NMP).
Temperature: 100–160 °C (oil bath or sealed tube) for 2–24 h.
Notes: C4 substitution generally precedes C6 under identical conditions.
Benzylic oxidation (C8–CH3)
SeO2 (0.5–1.5 equiv) in toluene or dioxane, 80–110 °C to give the aldehyde; or MnO2 under reflux for selective oxidation.
Directed benzylic metalation
LDA or LiTMP in THF at −78 to 0 °C, then electrophile (DMF, CO2, alkyl halides); strictly anhydrous, inert atmosphere.
Expected isolated yields vary widely (40–90%) depending on substitution, ligand, and scale; confirm with small-scale scouting.
Safety and Handling
Authoritative source: Always consult the SDS for 4,6-Dichloro-8-methylquinoline for definitive hazard, toxicological, and response information.
GHS information (from Product Data)
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-codes): Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General hazard considerations for halogenated quinoline derivatives (literature/good practice; not item-specific)
May cause irritation to skin, eyes, and respiratory tract; handle in a fume hood.
Avoid inhalation of dust and contact with skin/eyes; wash thoroughly after handling.
Potential aquatic toxicity is common for hydrophobic halogenated aromatics; prevent release to the environment.
PPE and engineering controls
Use lab coat, safety glasses or goggles, and suitable chemical-resistant gloves (e.g., nitrile). Work in a certified chemical fume hood.
Incompatibilities and reactivity (general)
Strong oxidizers may react with aromatic heterocycles; strong bases/nucleophiles can undergo SNAr on activated aryl chlorides under forcing conditions.
Avoid prolonged exposure to high temperatures; keep away from ignition sources as with most organic solids.
First-aid overview (general)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
For research use only; not for human or veterinary use.
Solvent Selection
This product is a heteroaromatic building block rather than a solvent. Solvent choice is typically driven by its use in transformations (e.g., SNAr, cross-coupling) and by dissolution behavior.
Polarity and dissolution (general trends for chloro-quinolines)
Expected to dissolve in polar aprotic media (DMF, DMAc, DMSO, NMP), chlorinated solvents (DCM, CHCl3), ethers (THF, 2-MeTHF), and aromatic hydrocarbons (toluene). Water solubility is expected to be low.
Selection by application
SNAr with amines: DMF/DMAc/NMP or DMSO; elevated temperature (100–160 °C) often required.
Suzuki–Miyaura: Dioxane/H2O, THF/H2O, or toluene/H2O with base (K2CO3, K3PO4, Cs2CO3). Micellar aqueous systems are feasible for greener practice.
Buchwald–Hartwig amination: Toluene, dioxane, CPME, or tert-amyl alcohol with soluble or supported bases.
Halogen–metal exchange or directed metalation on the benzylic site: Ethereal solvents (THF, MTBE) at low temperature.
Practical notes
Start with a minimal solvent screen: DMSO (solubilizing), DCM (workup/extraction), and a coupling solvent (dioxane or toluene). Confirm solubility at reaction temperature.
For scale-up, prefer higher-boiling, lower-toxicity options (e.g., 2-MeTHF, CPME) when compatible with the transformation.
Storage and Reconstitution
Storage conditions (from Product Data)
Store at room temperature.
Packaging/shipping
Shipped conditions: Not specified for this item; refer to CoA/Spec Sheet.
Stability and handling (general guidance)
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to heat and direct light. As with many aromatics, store away from strong oxidizers.
If long-term storage is anticipated, consider desiccation or inert-atmosphere storage to minimize adventitious moisture uptake and degradation, though quinoline chlorides are generally robust.
Reconstitution/stock solutions (general)
For reaction or screening stocks, prepare solutions in dry DMSO, DMF, THF, MeCN, toluene, or DCM, depending on the intended use. Filter if necessary to remove particulates.
For biological assays (where applicable to derivatives), dissolve first in a water-miscible organic solvent (DMSO/DMF) before dilution; verify solubility limits and compatibility.
Freeze–thaw guidance
Solid form: Not applicable. For solution stocks, aliquot to avoid repeated freeze–thaw. Store DMSO solutions at −20 °C protected from moisture.
For research use only.
Structure and Identity
Brief description: 4,6-Dichloro-8-methylquinoline is a dihalo-substituted quinoline scaffold bearing chlorine substituents at the 4- and 6-positions and a methyl group at the 8-position, offering two orthogonal aryl chloride handles on a bicyclic N-heteroaromatic core.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity details (labeled; not item specifications)
Likely molecular formula (derived from the name): C10H7Cl2N (literature/structure-derived)
Approx. molecular weight: ~212.07 g/mol (calculated from C10H7Cl2N)
Core scaffold: quinoline (benzopyridine), a fused bicyclic aromatic system (benzene fused to pyridine) with ring nitrogen at the 1-position of the quinoline numbering system.
Substitution pattern: chloro groups at positions 4 and 6 (on the benzopyridine ring system) and a methyl at position 8 (benzylic to ring junction). No stereocenters; fully aromatic planar framework.
2D structural description (verbal)
A pyridine ring fused to a benzene ring (quinoline). The ring nitrogen is part of the pyridine ring. Chlorine atoms are attached to the carbons para to the ring junction (C-4) and meta to the ring nitrogen on the benzene portion (C-6). A methyl group resides at C-8 adjacent to the ring junction on the benzene portion.
Synthetic Utility
Key functional elements of 4,6-dichloro-8-methylquinoline enable diverse transformations and modular library synthesis:
Dual aryl chlorides (C4, C6)
Pd-catalyzed cross-couplings: Suzuki, Buchwald–Hartwig, Sonogashira, and related carbon–heteroatom couplings. Ligand tuning allows selective activation of one C–Cl bond over the other, enabling stepwise diversification.
SNAr: The ring nitrogen enhances activation at C4 for nucleophilic substitution by amines, alkoxides, and thiolates; C6 substitution is also achievable under stronger conditions, supporting orthogonal installation of two distinct substituents.
8-Methyl (benzylic) position
Oxidation to aldehyde/acid or conversion to other functionalities provides handle for 8-position elaboration.
Benzylic metalation (e.g., with LDA) allows trapping with electrophiles (formylation, acylation, halogenation), expanding 3D diversity.
Quinoline nitrogen
Can be quaternized (e.g., MeI) to give quinolinium salts, useful as phase-transfer reagents, ligands, or further elaboration via Zincke-type chemistry.
Retrosynthetic value
Acts as a convergence point for building quinoline-based ligands, materials precursors, and bioactive analogs by leveraging orthogonal reactivity at C4/C6 and C8.
These modes collectively make this substrate an efficient hub for rapid SAR and scaffold diversification in medicinal and materials chemistry.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent.
No antigen/epitope, clone, isotype, or species reactivity data are associated with this item in the Product Data.
For target engagement studies, derivatized analogs of the quinoline scaffold are typically synthesized and profiled against specific biochemical targets.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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