Bithiophene-tri(ethyl ether) , CAS No.1636120-18-7

CAS: 1636120-18-7 Cat. No.: B1503799

Storage

Room temperature

Especificaciones

Condiciones de almacenamiento de almacenamiento

Room temperature

Application Protocols

No vendor-tested biological assay protocols are applicable. For materials processing, general practices include:

• Solution preparation: Dissolve the compound in a suitable organic solvent (e.g., toluene, chlorobenzene, CHCl3) with gentle warming if needed. Filter through 0.2 μm PTFE prior to coating.
• Thin-film deposition: Spin coat at 1000–3000 rpm depending on viscosity/solids loading; optimize bake/anneal temperatures to remove residual solvent without degrading the material.
• Purification: Silica gel chromatography with hydrocarbon/ether or hydrocarbon/chlorinated solvent mixtures; finalize with recrystallization if crystalline.

These are general literature practices; adapt conditions to your specific device architecture and characterization methods.

Biological Roles

This product is intended for materials science and synthetic applications. No biological role is specified.

• General context (informational)
  • Thiophene motifs occur in some pharmaceuticals and biomimetic materials, but bithiophene aryl ethers like this compound are primarily used in organic electronics and photonics research.
  • The compound is hydrophobic and not designed for biological systems; no metabolic or signaling function should be inferred.

For any work involving biological systems, assess solvent carrier effects and cytotoxicity independently; this product is sold strictly for research use in laboratory settings.

Buffer Applications

Not typically applicable. Bithiophene-tri(ethyl ether) is a hydrophobic organic building block with no acid/base buffering capacity in aqueous media. For practical usage, see the Solvent Selection and Reaction & Applications sections relevant to organic synthesis and materials processing.

Green Alternatives

When processing bithiophene-based materials, solvent choice dominates the environmental footprint.

• Greener processing options (general)

  • Favor aromatics like toluene or anisole over chlorinated solvents when solubility allows; they offer lower toxicity and better environmental profiles.
  • Consider 2‑MeTHF or CPME for certain syntheses and purifications; they can replace THF or DCM in some workflows while maintaining performance.
  • Supercritical CO2 or propylene carbonate may be explored for specialized deposition or cleaning steps, acknowledging solubility limitations for hydrophobic aromatics.

• Tradeoffs

  • High-boiling green solvents (anisole, propylene carbonate) may require elevated temperatures and longer drying times, impacting film morphology and throughput.
  • Chlorobenzene/o‑DCB often provide superior solubility and film quality for conjugated systems; greener substitutes may necessitate additives or co-solvent strategies.

Comparison (general purpose)

• Parameter | Conventional (CHCl3/DCM) | Greener option (toluene/anisole/2‑MeTHF)
• Solubility | Often excellent | Case-dependent; may need heat
• Toxicity | Higher | Lower
• Boiling point | Low–moderate | Moderate–high
• Film quality | Good but variable | Good; tuning may be needed

Choose the least hazardous solvent system that achieves required solubility and film performance.

Pharmaceutical Uses

Not applicable as a therapeutic agent or common excipient. Bithiophene-tri(ethyl ether) is a specialty research chemical for materials science and synthetic chemistry. It is not listed with pharmacopeial status. Any formulation-related handling should be limited to device/material contexts (e.g., organic electronics), not for human or veterinary administration.

Physical Properties

Item-specific specifications are not provided in the Product Data for this compound.

• Item-specific data

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for similar bithiophene aryl ethers (informational only)

  • Physical state: typically low-melting solids or viscous oils, depending on substitution pattern and purity.
  • Solubility: good in chlorinated solvents (e.g., CH2Cl2, CHCl3), aromatic solvents (toluene), and moderately polar aprotics (THF, DMF); negligible in water.
  • Thermal behavior: substituted bithiophenes usually show elevated thermal stability relative to unsubstituted thiophenes due to aryl-ether substitution; decomposition rather than sharp boiling under ambient pressure is common for higher MW derivatives.

Note: For precise, item-specific values, consult the Aladdin CoA/Specification Sheet and SDS.

Quality and Grades

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

• Interpreting grades (general guidance)

  • Research/technical grade: suitable for synthesis, materials R&D, and screening where trace impurities are tolerable.
  • High-purity/electronic grade (if applicable): favored for optoelectronic measurements (OFET/OPV/OLED) where trap states from impurities can affect performance; typically includes tighter metal and halide controls and low residual solvent.
  • HPLC grade (solvents) vs reagent grade (solids): for small-molecule building blocks like bithiophene derivatives, low UV background and metal content can be advantageous for spectroscopic characterization and device fabrication.

• Stabilizers/additives

  • Not specified for this item; refer to CoA/Spec Sheet. Aryl-ether bithiophenes are typically stable without inhibitors, but device-oriented use can benefit from additional purification (recrystallization, gradient sublimation) to remove trace oxidized species.

• Recommended quality assurance practices

  • Verify identity/purity by NMR (1H/13C), HRMS, and, where relevant, elemental analysis.
  • For device applications, consider additional purification and filtration through 0.2 μm PTFE prior to film formation to reduce particulates.

Reaction and Applications

• Materials science applications (general/literature)

  • Bithiophene derivatives are widely used as donor units in organic semiconductors (OFETs, OPV, OLED), hole-transport materials, and as comonomers in conjugated polymers. Ethoxy substitution increases solubility/processability and donates electron density, potentially raising HOMO levels relative to unsubstituted bithiophene.
  • Thin-film formation via spin coating or drop casting from aromatic/chlorinated solvents; thermal annealing can tune morphology and charge transport.

• Synthetic applications

  • Serve as precursors to brominated/iodinated monomers for cross-coupling polymerizations (Suzuki–Miyaura, Stille, Kumada). Aryl ether substituents typically survive these conditions.
  • Oxidative polymerization (e.g., FeCl3, SbCl5) can yield poly(bithiophene) derivatives; reaction selectivity depends on substituent regiochemistry.

• Practical tips (general)

  • Dry solvents and inert atmosphere are recommended during metal-catalyzed couplings to prevent catalyst deactivation and oxidative side reactions on electron-rich thiophenes.
  • For device fabrication, filter solutions (0.2 μm PTFE) before coating to remove particulates; control humidity to minimize film defects.

Note: Manufacturer-specified applications are not provided for this item; the above are typical literature uses for substituted bithiophene ethers.

Reaction Conditions

General literature guidance for reactions involving substituted bithiophenes (informational; adapt to your substrate and consult primary sources):

• Electrophilic halogenation

  • Reagents: NBS or NIS in DMF, CHCl3, or acetic acid.
  • Conditions: 0 °C to rt; 0.5–6 h; monitor by TLC/NMR to avoid over-bromination.

• Metal-catalyzed cross-coupling (for halogenated bithiophene derivatives)

  • Suzuki–Miyaura: Pd(PPh3)4 or Pd2(dba)3/XPhos; base K2CO3, Cs2CO3, or K3PO4; solvent toluene/THF/H2O or dioxane; 60–100 °C; 2–24 h.
  • Stille: Pd(PPh3)4; solvent toluene or DMF; 80–110 °C; 4–24 h. Exercise caution with organostannanes.
  • Kumada: Ni or Pd catalysts; THF/Et2O; 0–50 °C; fast reactions with Grignard reagents.

• Directed metalation/functionalization

  • Base: n‑BuLi or LiTMP; solvent THF; −78 to −40 °C; quench with electrophiles (B(OMe)3 for borylation, DMF for formylation, Me3SnCl for stannylation). Work under inert atmosphere.

• Oxidative polymerization

  • Oxidant: FeCl3 in CHCl3 or nitromethane; 0–25 °C; hours to overnight; quench with MeOH and wash thoroughly.

Yields and selectivity depend strongly on the substitution pattern and regiochemistry of Bithiophene-tri(ethyl ether); optimize on small scale before scale-up.

Safety and Handling

Safety overview for research use only (no medical/clinical use).

• Item-specific hazard information (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 guidance for aryl-ether bithiophene materials (informational)

  • Likely combustible organic solid/oil; keep away from ignition sources and hot surfaces. Avoid aerosol generation and dust.
  • Incompatibilities: strong oxidizers; strong electrophiles and halogenating agents may react with electron-rich thiophene rings.
  • Potential hazards: organic vapors/dust may irritate eyes, skin, and respiratory tract. Heated material may produce irritating fumes.

• PPE and hygiene

  • Wear safety glasses or goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust/vapors.
  • Wash hands thoroughly after handling; avoid contact with skin and eyes.

• First-aid (general)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; obtain medical advice.

Always consult the product SDS for authoritative hazard classification and emergency measures.

Solvent Selection

Bithiophene aryl ethers are generally nonpolar to moderately polar, hydrophobic organics.

• Polarity/miscibility (general/literature)

  • Expected to be insoluble in water; soluble in organic solvents such as chloroform, dichloromethane, chlorobenzene, toluene, xylene, THF, and possibly ethers like diethyl ether; solubility improves with temperature and depends on exact substitution pattern.
  • For thin-film processing (spin-coating, drop-casting), high-boiling aromatics (chlorobenzene, o-dichlorobenzene) often provide smooth films and adequate solubility.

• Selection tips by application

  • NMR: CDCl3, C6D6, or d8‑toluene are typical for aryl ethers; gentle heating may assist dissolution.
  • Purification: normal-phase silica gel chromatography with hexanes/EtOAc or hexanes/CH2Cl2 gradients; avoid overly polar eluents that can lead to tailing with sulfur-containing aromatics.
  • Film deposition: choose solvents matching desired evaporation kinetics and morphology; consider mixed solvents (e.g., toluene/mesitylene) to tailor drying profiles.

• Small comparison (general)

  • Chloroform: strong solubility, fast evaporation; less green, potential device residue.
  • Toluene: safer profile and good film quality; may require heating for full solubility.
  • o-DCB/chlorobenzene: high bp, excellent for slow-dry film formation; higher toxicity, more persistent.

Storage and Reconstitution

• Item-specific storage condition (from Product Data)

  • Store at room temperature.

• General storage guidance for aryl-ether bithiophenes

  • Keep tightly closed in a dry container; protect from moisture and prolonged light exposure to minimize slow oxidative discoloration.
  • Store under ambient inert atmosphere (nitrogen/argon) if long-term optoelectronic performance is critical.
  • Avoid strong oxidizers and halogenating agents in the storage area.

• Reconstitution/solution handling (general)

  • Prepare solutions in dry, oxygen-free solvents when intended for device fabrication; filter through 0.2 μm PTFE before use.
  • Typical solvent choices include toluene, chlorobenzene, o‑dichlorobenzene, CHCl3, or THF, depending on solubility requirements. Warm gently to aid dissolution; do not overheat.
  • For long-term solution storage, use amber glass, fill headspace with inert gas, and refrigerate if compatible with solvent to slow degradation.

Refer to the product CoA and SDS for item-specific stability and handling details. Research use only.

Structure and Identity

Brief overview: Bithiophene‑tri(ethyl ether) is a materials-science building block derived from a bithiophene core bearing three ethoxy substituents (literature naming implication). Exact regiochemistry and stereochemical assignment are not specified in the product data.

• Item-specific identifiers (from Product Data)

  • CAS: 1636120-18-7
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature description)

  • Core: a 2-ring thiophene system (bithiophene), conjugated and electron-rich.
  • Substituents: three ethoxy (–O–CH2CH3) groups attached to the thiophene ring carbons (positions not specified), increasing electron donation and solubility in organic media.
  • Functional groups: aryl ethers; thienyl C–S–C units; no stereocenters expected in the core.

• 2D structure in words (general)

  • Two five-membered thiophene rings connected through a C–C bond; three ring carbons bear ethoxy substituents. The ethoxy chains are flexible, non-conjugated pendants that do not disrupt the aromatic conjugation of the bithiophene backbone.

Synthetic Utility

• Functional group landscape

  • Electron-rich bithiophene core enables electrophilic substitution (e.g., halogenation) and metalation strategies; aryl ether substituents are generally robust under many cross-coupling conditions.
  • Ethoxy groups modulate solubility and electronics, aiding processability of downstream monomers/polymers.

• Representative transformations (general/literature)

  • Regioselective bromination/iodination (e.g., NBS/NIS or directed metalation) to prepare di/tri-halogenated monomers for Suzuki–Miyaura or Stille polymerizations.
  • Lithiation at activated positions using n‑BuLi or LiTMP at low temperature (often −78 °C) followed by electrophile quench (formylation, stannylation, borylation) to create versatile handles.
  • Oxidative coupling of thiophenes (FeCl3) to elongate conjugation; control over regioregularity depends on substitution pattern.

• Retrosynthetic value

  • The target can serve as an intermediate toward donor–acceptor small molecules by coupling bithiophene donors with acceptor cores (e.g., benzothiadiazole, diketopyrrolopyrrole).
  • Aryl ethers can be introduced via alkylation of hydroxy-thiophenes or via C–O cross-coupling (Ullmann/Chan–Lam) in precursor stages; they typically persist through later assembly steps.

Target Specificity

Not applicable. This product is a small-molecule materials building block, not a biological targeting reagent, antibody, or probe. No target, epitope, species reactivity, clone, or isotype information applies.

Preguntas frecuentes

How should this product be stored?

Store at room temperature.

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

The CAS Number is 1636120-18-7.

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.