4-(4-Ethoxyphenyl)pyridine - ≥95% , CAS No.4357-31-7

CAS: 4357-31-7 Cat. No.: E1309516 分子式: C₁₃H₁₃NO 分子量: 199.25

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

仕様と純度

≥95%

保管条件

Room temperature

入荷

Normal

純度

≥95%

名前と識別子

カノニカル・スマイル

CCOC1=CC=C(C=C1)C2=CC=NC=C2

IUPAC Name

4-(4-ethoxyphenyl)pyridine

InChIKey

YHUFCEAPVPUJHE-UHFFFAOYSA-N

INCHI

1S/C13H13NO/c1-2-15-13-5-3-11(4-6-13)12-7-9-14-10-8-12/h3-10H,2H2,1H3

分子量

199.25

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 分類 Pyridines and derivatives
      • Subclass Phenylpyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: Pyridines and derivatives
• Subclass: Phenylpyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyridines
• Alternative Parents: Phenoxy compounds Phenol ethers Alkyl aryl ethers Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 4-phenylpyridine - Phenoxy compound - Phenol ether - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Azacycle - Ether - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
• 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

化学的性質と物理的性質

• 分子量: 199.250 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 199.1 Da
• Monoisotopic Mass: 199.1 Da
• Topological Polar Surface Area: 22.100 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 169.000
• 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

No vendor-tested biological application protocols are specified for this item. Typical laboratory uses (literature/general) include:

• Synthetic transformations (ether deprotection, N-oxidation, metalation) as outlined in Reaction Conditions.
• Materials assembly via metal coordination employing the pyridinic nitrogen.

For chromatography and handling:

• Dissolve in an appropriate organic solvent (e.g., DCM, EtOAc, MeCN, or THF) for loading onto silica. If tailing is observed, add 0.1–1% triethylamine to the eluent to suppress pyridine–silica interactions.
• For analytical HPLC, use reversed-phase methods with MeCN/H2O + 0.1% formic acid or neutral buffers; expect poor retention at high organic content due to lipophilicity. Verify UV response around 254–280 nm typical of aryl pyridines (literature/general).

Biological Roles

This product is a synthetic heteroaromatic building block and is not known to have endogenous biological roles.

• General context (literature/general):

  • Aryl pyridines can interact with biological targets via the pyridinic nitrogen as a hydrogen-bond acceptor/ligating site, but 4-(4-ethoxyphenyl)pyridine is primarily used in chemical synthesis and materials research.
  • Neutral, lipophilic heteroarenes typically exhibit membrane permeability but limited aqueous solubility; any bioactivity would be structure- and context-dependent and is not implied here.

• Research use only: As stated in Product Data, this item is for research use only and not for human or veterinary use.

Buffer Applications

Not typically applicable. 4-(4-Ethoxyphenyl)pyridine is a neutral, poorly water-soluble organic compound and is not used as a buffering agent. For aqueous systems, consider true buffer components (e.g., phosphate, Tris, HEPES). If incorporating this molecule into biological assays, dissolve in a suitable co-solvent (e.g., DMSO or MeCN) and dilute into buffer with attention to final solvent percentage.

Green Alternatives

While the compound itself is a substrate, greener choices often concern the solvents and reagents used with it.

• Greener solvent swaps (general guidance):

  • Replace DCM with EtOAc, 2-MeTHF, or CPME where feasible (extractions, chromatography, reactions).
  • Replace DMF/NMP with MeCN, propylene carbonate, Cyrene, or green amide alternatives (PolarClean) when compatible with the reaction.
  • Use 2-MeTHF or CPME instead of THF/toluene for many organometallic and catalytic couplings due to better safety and biorenewable content (2-MeTHF).

• Greener reagents for key transformations (general):

  • O-Dealkylation: Consider catalytic transfer dealkylations or oxidative demasking methods instead of stoichiometric halophiles (e.g., BBr3), when compatible with the substrate.
  • Oxidations to N-oxides: Use H2O2/AcOH or urea–hydrogen peroxide as safer oxidants in place of peracids.

• Trade-offs:

  • Greener solvents may change solubility and rates; re-optimize catalyst loadings and temperatures.
  • Some biorenewable ethers (2-MeTHF) contain water/peroxides as received; ensure proper drying and inhibitor control as needed.

• Mini comparison (general):

  • THF vs 2-MeTHF: similar polarity; 2-MeTHF offers higher boiling point and improved phase separation, but can be less miscible with water—beneficial for workups.

Pharmaceutical Uses

No pharmacopeial or excipient role is specified for this item; refer to CoA/Spec Sheet.

• General context (literature/general):
  • Aryl–pyridine motifs are common in medicinal chemistry as scaffolds or intermediates during hit-to-lead optimization.
  • The ethoxy substituent can serve as a latent phenol (via dealkylation), enabling prodrug or protecting-group strategies in synthetic routes, but this product is offered strictly for research and process development use, not for clinical applications.

Physical Properties

• Item-specific values from Product Data: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed descriptors (informational; not product specifications):

  • Exact mass (C13H13NO): 199.0997 Da (computed)
  • H-bond donors: 0; H-bond acceptors: 2 (pyridine N, ether O) (computed)
  • Rotatable bonds: 3 (biaryl bond + ethoxy C–C) (computed)
  • Aromatic rings: 2 (general)
  • Polar surface area (TPSA): ~17–25 Ų (typical for one pyridine N + ether O; computed estimates vary)
  • LogP: typically in the 2–3 range for para-ethoxy arylpyridines (literature/general; method-dependent)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling/Melting points, density, refractive index, UV-Vis: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (general expectation): soluble in common organic solvents (e.g., DCM, THF, toluene, EtOAc, MeCN) and in polar aprotic media (DMF, DMSO); negligible water solubility (literature/general for neutral arylpyridines with one ether).

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades (general guidance):

  • Research grade: suitable for synthetic and analytical research applications; typical impurity limits vary by vendor and lot.
  • Purified/assay specifications: If GC/LC purity, water, or residual solvent specs are critical for your work (e.g., catalysis, materials), consult the CoA for the exact assay method and thresholds.
  • Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Aryl ethers and arylpyridines usually do not require stabilizers, but lots can differ.

• Practical QA considerations (general):

  • Lot-to-lot verification: check NMR (1H/13C) for biaryl coupling patterns and characteristic ethoxy signals (CH3 triplet ~1.3–1.4 ppm, CH2 quartet ~4.0–4.2 ppm; literature/general) and pyridine aromatic resonances (~7–9 ppm).
  • Trace metal content: Not specified for this item; refer to CoA/Spec Sheet if using in metal-catalyzed reactions or electronic materials.
  • UV background: Not specified; if using for photophysical studies, request UV-Vis/HPLC trace from the lot CoA.

Reaction and Applications

This para-aryl–pyridine is a versatile building block in heteroaryl materials, ligand design, and late-stage diversification.

• Representative applications (literature/general):

  • O-dealkylation to the phenol: Ethoxy → phenol via BBr3 or AlCl3/thiophenol systems, affording 4-(4-hydroxyphenyl)pyridine as a gateway to ethers/esters/aryl carbonates.
  • N-oxidation: Formation of the pyridine N-oxide (mCPBA, H2O2/AcOH), enabling directed ortho C–H functionalization on the pyridine ring.
  • Electrophilic substitution on the phenyl ring is deactivated by the para-ethoxy/biaryl array; however, metalation (e.g., ortho-lithiation adjacent to the ether under strong base) followed by electrophile quench can be viable.
  • Cross-coupling from halogenated derivatives: While the title compound lacks a halogen, it serves as a reference core for constructing donor–acceptor systems (Suzuki, Negishi, Kumada) when pre-functionalized.
  • Coordination chemistry/materials: The pyridyl nitrogen can coordinate to metals (Zn2+, Pd2+, Ir3+, etc.), useful for MOFs, OLED ligands, and supramolecular assemblies.

• Practical notes:

  • Ether stability: Generally robust under neutral/basic conditions; avoid strong Brønsted/Lewis acids if retention of the ethoxy is required.
  • Purification: Aromatic ethers and pyridines elute with moderately polar eluents (e.g., hexanes/EtOAc 3:1 to 1:1); add 0.1–1% NEt3 to suppress pyridine–silica interactions if tailing occurs.

Reaction Conditions

General guidance for common transformations of aryl–pyridines and aryl ethers (literature examples; adjust to your substrate and scale):

• O-Dealkylation (ether → phenol):

  • Reagents: BBr3 (1–3 equiv per OEt), solvent CH2Cl2 or toluene, 0 °C to rt, 1–16 h; quench cautiously with MeOH/H2O.
  • Alternative: AlCl3/thiophenol or TMSI in acetonitrile; 0–25 °C.

• N-Oxidation (pyridine → N-oxide):

  • mCPBA (1.1–1.5 equiv), CH2Cl2, 0 °C to rt, 1–4 h; or H2O2/AcOH, 40–60 °C.

• Directed ortho C–H functionalization (via N-oxide):

  • Pd- or Rh-catalyzed acylation/arylation in polar aprotic solvents (DMF/MeCN), 60–120 °C; bases such as NaOAc/K2CO3; O-directed selectivity on the pyridine ring.

• Ortho-lithiation near the ethoxy on the phenyl ring:

  • s-BuLi (1.1–1.5 equiv) with TMEDA in THF, −78 to −40 °C, then electrophile (e.g., CO2, I2, trialkylstannyl chloride); work up at low temperature to minimize rearrangements.

• Coordination assembly:

  • Mix with metal salts (e.g., Zn(II), Pd(II)) in MeOH/MeCN or DMF to form adducts/coordination polymers; monitor by 1H NMR/ESI-MS.

Note: Conditions above are literature-general and not specifications for this item. Optimize stoichiometry, temperature, and time based on scale and desired selectivity. Always assess compatibility of the ethoxy and pyridine nitrogens with strongly acidic or Lewis acidic systems.

Safety and Handling

• GHS information from Product Data: Not specified for this item; refer to the product SDS for authoritative hazard classification, GHS pictograms, Signal Word, and H-statements.

• General safety guidance (literature/general for neutral arylpyridines and aryl ethers):

  • Likely to be combustible; avoid ignition sources and excessive heat. Handle away from strong oxidizers and strong acids (which may protonate the pyridine nitrogen) or strong Lewis acids/halophiles (which can promote ether cleavage).
  • Potential irritant to skin, eyes, and respiratory tract. Use PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of vapors or dust/aerosols.
  • First aid (general): On skin/eye contact, rinse with plenty of water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested or if symptoms persist, seek medical attention. Always consult the SDS for detailed measures.
  • Spill/cleanup: Absorb liquid with inert material or collect solids without raising dust; ventilate area and dispose according to local regulations.
  • Incompatibilities: Strong oxidizing agents; strong acids or bases that may cause degradation (e.g., acid-catalyzed ether cleavage under harsh conditions). No specific peroxide-forming hazard is expected for aryl ethers compared to dialkyl ethers.

• Storage and transport (from Product Data):

  • Storage: Room temperature.
  • Shipped: Normal.

Solvent Selection

As a neutral, moderately lipophilic heteroaromatic, 4-(4-ethoxyphenyl)pyridine dissolves well in many organic media.

• Polarity class (general): moderately nonpolar to polar aprotic soluble; poor water solubility expected.
• Recommended solvents (literature/general):
  • Good: DCM, EtOAc, toluene, THF, MeCN, acetone.
  • For high concentrations or high-T chemistry: DMF, DMAc, NMP, DMSO.
• Dielectric/miscibility (general):
  • Use polar aprotics (DMF/DMSO/MeCN) to aid solubility for transition-metal catalysis or C–H activation.
  • Use less polar solvents (toluene/THF) for base-sensitive transformations or where high volatility is preferred.
• Practical tips:
  • Ensure water-free media for air/moisture-sensitive couplings; dry with 3Å/4Å sieves or distill solvent as needed.
  • For crystallization, binary systems such as EtOAc/hexanes or toluene/hexanes often provide tunable solubility for arylpyridines (optimize empirically).
• Comparison (general):
  • Versus more polar pyridinium salts, this neutral compound offers broader solubility in less polar solvents, aiding purification by silica gel chromatography.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature.
• Shipping (item-specific): Normal.
• Reconstitution: Not applicable to this neat chemical. If preparing stock solutions, use dry, compatible organic solvents (e.g., DMSO, MeCN, THF, or DCM) and store solutions in tightly sealed amber vials under inert gas if long-term stability is required.
• Stability considerations (general):
  • Aryl ethers and pyridines are typically stable to air and ambient light; protect from strong acids, moisture in reactive operations, and prolonged high heat.
  • Avoid contact with strong oxidizers. If using highly acidic conditions, consider potential ether cleavage.
• Packaging: Keep container tightly closed. Use septum-sealed vials for air/moisture-sensitive manipulations in catalytic reactions.
• Research Use Note: For research use only.

Structure and Identity

A para-aryl–pyridine building block featuring an ethoxy-substituted phenyl ring connected to the 4-position of pyridine.

• Item-specific identifiers from Product Data:

  • CAS: 4357-31-7
  • SKU: E1309516
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (informational):

  • Typical molecular formula (literature): C13H13NO
  • Typical molecular weight (literature): ~199.25 g/mol
  • Example SMILES (literature): CCOc1ccc(cc1)c2ccncc2 (para-ethoxyphenyl linked to pyridin-4-yl)
  • Core structural features: one pyridine ring (sp2 N), one para-ethoxy-substituted phenyl ring; biaryl C–C bond at the 4-position of the pyridine and the 1-position of the phenyl; one ether (Ar–O–Et).

• 2D structure description (general):

  • A six-membered aromatic ring bearing a ring nitrogen (pyridine) is para-coupled through a C–C bond to a phenyl ring. The phenyl ring carries an ethoxy substituent para to the biaryl bond. No stereocenters are present; the molecule is achiral and planar/near-planar around the biaryl axis.

Synthetic Utility

Key reactivity arises from three functional elements: the pyridinic nitrogen (basic/ligating), the biaryl C–C bond (handles for further substitution via directed methods), and the aryl–O–Et ether (a transformable protecting group).

• Transformations (literature/general):

  • Ether → phenol: BBr3 or BCl3 (0 to −78 °C), or AlCl3-mediated systems; phenol then participates in etherification, esterification, or carbonate formation.
  • N-oxidation to pyridine N-oxide, enabling directed ortho C–H activation (e.g., acylation/arylation) on the pyridine ring.
  • Metalation: Directed ortho-metalation adjacent to the ether on the phenyl ring under strong bases (s-BuLi/TMEDA), followed by electrophile trapping.
  • Quaternization: Alkylation of the pyridine nitrogen to form pyridinium salts, tuning solubility/electronic properties.
  • Cross-coupling on derivatives: Halogenate or borylate the ring(s) in subsequent steps to access broader substitution patterns via Suzuki–Miyaura, Buchwald–Hartwig, or Chan–Lam couplings.

• Retrosynthetic value:

  • Serves as a convergent intermediate in donor–acceptor materials (ethoxyphenyl = donor; pyridyl = acceptor) and as a precursor to para-hydroxy analogs without exposing sensitive phenols earlier in a route.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not have target specificity data such as antigen, epitope, clone, or isotype. For binding or biological target information, consult primary literature specific to your application.

よくある質問

What is the purity of this product?

This product is supplied at ≥95% 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 4357-31-7, the molecular formula is C13H13NO, and the molecular weight is 199.25 g/mol. InChIKey YHUFCEAPVPUJHE-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.