4-Bromo-6-ethoxyquinoline - ≥97% , CAS No.1070879-28-5

CAS: 1070879-28-5 Cat. No.: B1305983 Summenformel: C₁₁H₁₀BrNO Molekulargewicht: 252.11 PubChem CID: 39346123

GRADE & PURITY ≥97%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥97%

Namen und Kennungen

Kanonisches Lächeln

CCOC1=CC2=C(C=CN=C2C=C1)Br

IUPAC Name

4-bromo-6-ethoxyquinoline

InChIKey

PQVJAYWECGRXLH-UHFFFAOYSA-N

INCHI

1S/C11H10BrNO/c1-2-14-8-3-4-11-9(7-8)10(12)5-6-13-11/h3-7H,2H2,1H3

Isomere SMILES

CCOC1=CC2=C(C=CN=C2C=C1)Br

PubChem CID

39346123

Molekulargewicht

252.11

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Quinolines and derivatives
• Subclass: Haloquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Haloquinolines
• Alternative Parents: Phenol ethers Alkyl aryl ethers Pyridines and derivatives Aryl bromides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Haloquinoline - Phenol ether - Alkyl aryl ether - Aryl bromide - Aryl halide - Pyridine - Benzenoid - Heteroaromatic compound - Ether - Azacycle - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound
• Beschreibung: 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

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: 252.110 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 250.995 Da
• Monoisotopic Mass: 250.995 Da
• Topological Polar Surface Area: 22.100 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 188.000
• 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

Not applicable to this product type.

• No tested bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are applicable to a small-molecule reagent of this class.
• For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for representative procedures.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

• General context (literature/general, not a medical claim):

  • Quinolines are prevalent in natural products and functional materials and often serve as privileged scaffolds in chemical biology probes and coordination ligands.
  • The ring nitrogen can participate in metal coordination (e.g., to Zn2+, Cu2+), and the extended aromatic system provides UV absorption and potential fluorescence, which can be useful for assay development or probe design.
  • 4-Bromo-6-ethoxyquinoline itself is primarily a synthetic intermediate; any biological activity would derive from derivatives prepared from this handle (e.g., 4-substituted quinolines).

This product is designated for research use only.

Buffer Applications

This compound is a neutral organic heteroaromatic building block and is not used as a buffering agent.

• Not typically applicable: It does not form defined buffer systems in aqueous media.
• Practical note: If preparing stock solutions for biochemical assays, dissolve in DMSO or DMF and dilute into assay buffer, keeping final cosolvent ≤1–2% v/v as assay tolerates.

Green Alternatives

• Greener coupling media (literature/general):

  • Replace dioxane/DMF with 2-MeTHF, CPME, or aqueous micellar systems (e.g., TPGS-750-M) for Suzuki/Buchwald reactions. These can reduce VOC impact and facilitate phase separations.
  • Use ethanol/water or isopropanol/water in combination with modern ligands/catalysts for certain Suzuki couplings.

• Greener leaving groups/building blocks (general):

  • Where feasible, 4-chloro-6-ethoxyquinoline may be used with highly active catalysts (e.g., BrettPhos-type ligands) to avoid bromide waste; performance can be substrate- and scale-dependent.
  • Employ organoboron partners that are stable and low-toxicity (MIDA boronates, pinacol boronates) instead of stannanes.

• Comparative considerations (general):

| Choice | Benefit | Trade-offs | |---|---|---| | 2-MeTHF vs dioxane | Bio-based, lower toxicity, good for aqueous biphasic Suzuki | Water content/peroxide control; slightly different solubility | | Micellar catalysis (H2O) | Minimal organic solvent, simplified workup | Surfactant sourcing/removal; catalyst compatibility | | Aryl chloride instead of bromide | Less halogenated waste | Requires more active catalysts/conditions |

Adopt process-intensification tools (flow chemistry, solvent recycling) to further reduce environmental footprint.

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• General non-clinical context (literature/general):

  • Used as a synthetic intermediate for generating 4-substituted quinoline libraries during hit-to-lead campaigns and SAR exploration.
  • The aryl bromide handle enables modular installation of pharmacophores via Suzuki, Buchwald–Hartwig, or alkynylation, facilitating rapid analog generation.
  • Not intended for human or veterinary use; no therapeutic claims are made for this material.

For GMP or regulatory-enabled manufacturing, ensure sourcing, impurity profiles, and residual metal limits meet the project’s quality system requirements.

Physical Properties

• Item-specific values from Product Data:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature values (for general reference; not item specifications):

  • Approximate formula and MW: C11H10BrNO, ~252.11 g/mol (computed from atom counts)
  • Physical state/solubility tendency (literature/general): Typically a crystalline solid for comparable quinoline aryl bromides; sparingly soluble in water; soluble in common organic solvents such as DCM, chloroform, THF, DMF, DMSO, toluene, and EtOAc. Solubility increases in polar aprotic media (DMF/DMSO) and on gentle warming.
  • Acid/base character (general): Weakly basic heteroaromatic (pyridine-type N); can form protonated salts with strong acids.
  • Volatility: Low (aromatic bromides are generally non-volatile under ambient conditions).

Notes: Do not treat the above as product specifications; consult the CoA/Spec Sheet for item-specific data (mp, purity, residual solvents, etc.).

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grades (general guidance):

  • Research/technical grade typically indicates suitability for synthetic and discovery workflows, with impurity profiles appropriate for organic synthesis.
  • HPLC or LC/MS grades (when applicable) emphasize low UV background and minimal nonvolatile residues for analytical applications.
  • Stabilizers: None indicated in Product Data. If a stabilizer or inhibitor is present for a different lot, it will be declared on the CoA; its presence can influence reactivity (e.g., in cross-couplings) and may require pre-purification.

• Recommended quality checks for this scaffold (general):

  • Identity: 1H/13C NMR and HRMS. The aryl bromide carbon typically appears downfield in 13C NMR; quinoline N influences chemical shifts (pyridine region).
  • Purity: HPLC/UPLC with diode-array detection (monitor 210–350 nm due to quinoline chromophore). GC may be limited by thermal stability.
  • Residual metals/halides: If used in metal-catalyzed reactions, post-reaction materials should be checked for Pd/Cu residues when relevant.

Refer to the Aladdin CoA/Spec Sheet for this item’s exact assay, impurity limits, and analytical methods.

Reaction and Applications

As a 4-bromo-quinoline bearing an electron-donating ethoxy group at C-6, this scaffold is well-suited for cross-coupling and late-stage diversification.

• Cross-coupling (literature/general):

  • Suzuki–Miyaura: Couples with boronic acids/esters to introduce aryl/alkenyl substituents at C-4. Typical systems: Pd(dppf)Cl2, Pd-PEPPSI, or Pd2(dba)3 with SPhos/XPhos; bases like K2CO3, K3PO4, Cs2CO3; solvents 1,4-dioxane/H2O, toluene/H2O, or 2-MeTHF/H2O.
  • Buchwald–Hartwig amination: Installation of (hetero)arylamines or alkylamines at C-4 using Pd catalysts (e.g., Pd2(dba)3 with BrettPhos or RuPhos) and strong bases (NaOtBu, Cs2CO3).
  • Sonogashira: Alkyne introduction with Pd/Cu catalysis in amine or amine-free protocols; use degassed solvents.
  • Stille/Negishi: Alternative organometallic partners when boron-based reagents underperform.

• Directed metalation/halogen–metal exchange (general):

  • Lithium–halogen exchange at C-4 with n-BuLi or t-BuLi at −78 °C in THF enables formylation (DMF), carboxylation (CO2), or electrophile trapping.

• Electrophilic/nucleophilic aromatic chemistry (general):

  • The quinoline N deactivates the adjacent ring toward electrophiles yet can direct metalation. The 6-ethoxy substituent influences regioselectivity and electronics, sometimes facilitating C–O cleavage under strong conditions (e.g., demethylation analogs).

• Applications:

  • Preparation of substituted 4-aryl/alkenyl/alkynyl quinolines for materials, ligand design, and medicinal chemistry SAR.
  • Heteroaryl core for photophysical studies due to quinoline chromophore.

Reaction Conditions

General literature guidance for representative transformations of aryl-bromide quinolines (not item-specific specifications):

• Suzuki–Miyaura coupling (C-4):

  • Catalyst/ligand: 1–3 mol% Pd(dppf)Cl2·DCM or Pd2(dba)3 (1 mol% Pd) with SPhos/XPhos (2–4 mol%).
  • Base: K3PO4 (2–3 equiv) or Cs2CO3 (2 equiv).
  • Solvent: 1,4-dioxane/H2O (4:1) or 2-MeTHF/H2O; 70–100 °C; 2–12 h.
  • Notes: Degas solvents; add aqueous phase last to minimize proto-debromination. Typical isolated yields for similar substrates: 70–95% (literature ranges).

• Buchwald–Hartwig amination:

  • Pd source: Pd2(dba)3 (1 mol% Pd) or Pd(OAc)2 (2 mol%). Ligands: BrettPhos, t-BuBrettPhos, or RuPhos (2–4 mol%).
  • Base: NaOtBu or Cs2CO3 (2–3 equiv).
  • Solvent: Toluene, 1,4-dioxane, or t-AmOH; 80–110 °C; 4–18 h.
  • Notes: For aliphatic amines, biaryl phosphines excel; for anilines, use stronger bases and higher temperatures.

• Sonogashira alkynylation:

  • Pd(PPh3)2Cl2 (1–2 mol%), CuI (5–10 mol%), Et3N or DIPEA; THF or DMF; rt–60 °C; 2–8 h. Copper-free variants use XPhos-type ligands.

• Halogen–lithium exchange:

  • n-BuLi (1.1–1.3 equiv) in anhydrous THF at −78 °C; trap with DMF (formylation) or CO2 (carboxylation); then warm to 0 °C and quench.

• Analytical monitoring:

  • LC–MS (ESI+) for rapid tracking; strong UV response at 254–320 nm enables HPLC monitoring.

Adjust catalyst loadings and temperatures based on substrate solubility and scale.

Safety and Handling

• Item-specific hazard information from Product Data:

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

• General safety guidance for halogenated heteroaromatics (literature/general; defer to SDS for authoritative details):

  • Likely hazards: May cause skin/eye irritation and respiratory tract irritation. Dust may be harmful if inhaled. Combustible dust risk if finely divided.
  • PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust/vapors, particularly during heating or reaction workups.
  • Handling: Avoid generating dust. Prevent contact with strong oxidizers and strong bases/acids during storage. When weighing, use antistatic measures and a draft-shielded balance cup.
  • First aid (overview): Eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air; seek medical attention if symptoms persist. Ingestion—not intended for use; rinse mouth, seek medical attention.
  • Fire safety: Use CO2, dry chemical, or foam. Thermal decomposition can release hydrogen bromide and nitrogen oxides; firefighters should wear SCBA.
  • Waste: Collect halogenated organic waste separately in accordance with institutional and regulatory guidance.

Always consult the product SDS for definitive hazard classification and response procedures.

Solvent Selection

This compound is a nonpolar-to-moderately polar heteroaromatic solid with low aqueous solubility and good solubility in organic media.

• General miscibility/solubility (literature/general):

  • Polar aprotic: Good solubility in DMF, DMAc, NMP, DMSO (useful for high-temperature couplings).
  • Ethers/aromatics: Soluble in THF, 2-MeTHF, dioxane, toluene, and chlorinated solvents (DCM/CHCl3).
  • Alcohols: Moderate solubility in MeOH/EtOH; may hydrogen-bond via ring N.
  • Water: Poorly soluble.

• Selection tips for applications:

  • Pd-catalyzed couplings (Suzuki/Buchwald-Hartwig): 1,4-dioxane, toluene, or 2-MeTHF often with aqueous base; DMF/DMAc/NMP for tougher substrates.
  • Lithiation/halogen–metal exchange: Anhydrous THF, 2-MeTHF, or CPME at low temperature.
  • Nucleophilic substitutions/SNAr on the quinoline (when feasible): Polar aprotic solvents (DMSO/DMF) enhance rates.

• Comparison (general):

  • Toluene: Higher thermal stability, easy workup; lower polarity may limit solubility.
  • Dioxane/2-MeTHF: Good for mixed aqueous systems in Suzuki; 2-MeTHF provides a greener alternative with similar performance.
  • DMF/DMAc/NMP: Excellent solvating power; consider higher boiling points and regulatory profiles during scale-up.

Storage and Reconstitution

• Item-specific storage/shipping (from Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Normal

• General storage guidance (literature/general):

  • Keep tightly closed in a dry, well-ventilated place. Protect from prolonged light and moisture. Store away from strong oxidizers and strong acids/bases.
  • If long-term storage is anticipated, consider an amber container or secondary light protection due to the quinoline chromophore.

• Reconstitution and solution handling (general):

  • Stock solutions: Prepare in dry organic solvents such as DMSO, DMF, THF, CHCl3, or toluene. Filter through a PTFE syringe filter if particles persist.
  • Typical concentrations: 10–100 mM in DMSO or DMF for library synthesis; adjust based on solubility and intended use.
  • Stability of solutions: Store refrigerated (2–8 °C) in amber vials; use within days to weeks depending on solvent and headspace oxygen. For sensitive cross-coupling, prepare fresh solutions.

For exact item-specific stability, water content, and purity, consult the CoA/Spec Sheet. Research use only.

Structure and Identity

A halogenated, ether-substituted quinoline building block useful for cross-coupling and heteroarene functionalization.

• Item-specific identifiers (from Product Data):

  • SKU: B1305983
  • Product Name: 4-Bromo-6-ethoxyquinoline
  • CAS: 1070879-28-5
  • InChIKey: 284700 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structural information (for reference; not item-specific specs):

  • Core scaffold: Quinoline (benzannulated pyridine) bearing a bromine at C-4 and an ethoxy substituent at C-6 of the quinoline framework.
  • Functional groups: Aryl bromide (C–Br on an electron-deficient heteroaromatic), aryl ether (–OCH2CH3), and a ring nitrogen (pyridine-type) within the quinoline.
  • Molecular formula (literature/computed): C11H10BrNO
  • Molecular weight (literature/computed): ~252.11 g/mol
  • 2D description: A fused bicyclic aromatic system (pyridine fused to benzene). The ring nitrogen is in the pyridine portion. The bromine is para to the ring junction on the pyridine ring (position 4), and the ethoxy group resides on the benzene portion at position 6.

• Stereochemistry: None (achiral, planar aromatic system).

Synthetic Utility

• Key reactive sites (general):

  • C-4 Aryl bromide: Amenable to Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig, Sonogashira, Stille, Negishi) and halogen–lithium exchange.
  • Ring nitrogen: Can be quaternized (N-alkylation) to form quinolinium salts, modifying solubility and electronics.
  • Ethoxy group: Under strong conditions, can undergo O-dealkylation or serve as a leaving group after activation (e.g., demethylation analogs suggest potential).

• Retrosynthetic value (general):

  • A convergent branch point for constructing 4-substituted quinoline frameworks from a single electrophile, enabling rapid diversification at C-4 while preserving the 6-ethoxy motif.

• Downstream transformations:

  • Carbon–carbon: Install biaryl, styryl, or alkynyl units; subsequent oxidation/reduction or cyclizations expand chemical space.
  • Carbon–heteroatom: Amination to give anilines/anilides; etherification or thioether formation via coupling with alkoxides/thiolates (with appropriate catalysts).
  • Directed ortho-metalation adjacent to the ring nitrogen enables further substitution patterns on the benzannulated ring.

• Purification/workup tips (general):

  • Quinoline chromophore aids UV monitoring (254–300 nm). Avoid basic alumina for sensitive Pd-coupled products; use silica gel with 0.1–1% Et3N if amination products streak.

Target Specificity

Not applicable to this product type.

• This item is a small-molecule heteroaromatic building block and does not possess biological target specificity, clone information, or isotype data.
• No antigen/epitope details are provided in the Product Data.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1070879-28-5, the molecular formula is C11H10BrNO, and the molecular weight is 252.11 g/mol. InChIKey PQVJAYWECGRXLH-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.