[2,2'-Bithiazole]-5,5'-dicarboxaldehyde , CAS No.259542-09-1

CAS: 259542-09-1 Cat. No.: B1504507

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Application Protocols

No tested biological or analytical application protocols are provided for this item. For synthetic uses, follow the general reaction guidelines in the Reaction Conditions tab and adapt to your specific substrates and scale. For thin-film fabrication, determine a solvent/temperature profile that achieves complete dissolution and uniform casting (e.g., chlorobenzene or o-dichlorobenzene, if compatible).

Biological Roles

This product is a synthetic heteroaromatic dialdehyde intended for materials and synthetic chemistry research. It is not a natural metabolite, cofactor, or biomacromolecule.

• Biological function: No established biological role; not intended for biological systems.
• Reactivity in bioconjugation (general): The aldehyde groups can, in principle, form imines (Schiff bases) with primary amines on biomolecules under controlled conditions, but such use requires careful control of pH and is outside typical applications for this building block.

For research use only; not for use in diagnostic, therapeutic, or clinical applications.

Buffer Applications

Not typically applicable. As a hydrophobic heteroaromatic dialdehyde with poor water solubility, this compound is not used to prepare aqueous buffers. If aqueous handling is required for a specific experiment, dissolve first in a water-miscible organic co-solvent (e.g., DMSO) and then dilute into the target medium, verifying stability and avoiding amine-containing buffers that can form imines.

Green Alternatives

Greener choices focus on solvent and process selection, since the core building block is structurally defined.

Greener solvent strategies (general):

• Replace DMF/DMAc/NMP with safer polar media where feasible: Cyrene (dihydrolevoglucosenone), propylene carbonate, or dimethyl sulfoxide combined with water-removal strategies.
• Swap chlorinated processing solvents with higher-boiling, less hazardous aromatics (toluene, anisole) or esters (ethyl acetate) when solubility allows.
• For imine/COF synthesis, use ethanol or green solvent mixtures with catalytic acid and Dean–Stark (toluene) rather than neat high-boiling amides.

Small comparison (general, not item-specific specifications):

• DMF/NMP: excellent solubility and reaction control; reproductive toxicity concerns; difficult removal.
• DMSO: good solvency; benign profile; higher boiling complicates drying.
• Cyrene/PC: greener alternatives; compatibility varies, may require optimization of base/catalyst systems.
• Chlorobenzene/o-DCB: device-relevant film quality; environmental/health burdens—consider anisole or mesitylene if dissolution is sufficient.

Process intensification:

• Employ solvent recycling and reduced solvent volumes via concentrated reactions.
• Use solid-state or mechanochemical condensation (ball milling) for Schiff base formation when feasible, minimizing solvent use.

Always validate that greener substitutions preserve reaction performance and material properties.

Pharmaceutical Uses

Not applicable to this product. This heteroaromatic dialdehyde is offered for research and materials science applications and is not used as an excipient or pharmacopoeial substance. No pharmacopeia status or formulation role is provided. For research use only.

Physical Properties

Item-specific physicochemical specifications (mp, bp, density, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for this class (for planning only, not specifications):

• Aggregate state: Typically a yellow to orange crystalline solid for conjugated bithiazole dialdehydes.
• Solubility profile: Poorly soluble in water; soluble to moderately soluble in polar aprotic solvents (DMSO, DMF, NMP) and in chlorinated aromatics (chlorobenzene, o-dichlorobenzene). Solubility in common ethers and esters may be modest and temperature-dependent.
• Polarity/partitioning: Dialdehyde functionality increases polarity relative to hydrocarbon analogs, but the extended π-system and heteroaromatics impart significant organic solvent affinity.
• Optical properties: Conjugated bithiazoles often show UV–vis absorption in the near-UV to visible range due to π–π* transitions; exact λmax and ε are structure- and solvent-dependent and should be measured for your batch.

Do not treat the above as product specifications. Verify working properties (solubility, λmax) empirically in your intended solvent system.

Quality and Grades

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

Guidance on grades (general):

• Research grade: Suitable for synthesis and materials R&D; may not include low-UV or trace-metal specifications.
• High-purity or electronic grades (if applicable to a batch): Target low metal and ionic contaminants for optoelectronic applications; often accompanied by ICP and residual solvent data.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Aldehyde stabilizers are uncommon; quality is typically maintained by dryness and protection from prolonged air/light exposure.

Verification and documentation:

• For reproducible device/synthesis performance, request and retain the batch CoA including purity assay (e.g., HPLC/GC/NMR), residual solvents, and water content where measured. If your application is chromatography- or optics-sensitive, consider running UV–vis baselines and 1H NMR to confirm absence of hydrate/polymerization.

Batch-to-batch considerations (general):

• Dialdehydes can undergo slow surface oxidation or hydrate formation; gentle drying under vacuum prior to critical reactions may improve consistency.

Reaction and Applications

Manufacturer category indicates materials science. As a 5,5′-dialdehyde on a 2,2′-bithiazole core, this building block is well-suited for constructing extended π-systems and functional frameworks.

Representative application families (general/literature):

• Schiff base/imine formation with primary amines or diamines to access linear diimines, macrocycles, and covalent organic frameworks (COFs). The electron-deficient bithiazole core promotes planarity and π–π stacking in the resulting materials.
• Knoevenagel condensations with active methylene compounds (e.g., malononitrile, cyanoacetates) to create push–pull olefins and acceptor–acceptor segments for n-type conjugated polymers and small-molecule acceptors.
• Wittig and Horner–Wadsworth–Emmons olefinations to extend conjugation symmetrically from both aldehyde termini; useful for tuning band gaps and LUMO levels in organic electronic materials.
• Oxime/hydrazone formation for dynamic covalent chemistry and surface immobilization.
• Reductive amination to generate diamines on a bithiazole backbone, enabling further coupling (amide formation, urea linkages).
• Polymer chemistry: As a bifunctional node for step-growth polymerizations (e.g., imine-linked, acetal-linked under acid catalysis) yielding ladder-like or network structures with high thermal stability.

Practical tips:

• Maintain anhydrous conditions for base- or nucleophile-sensitive transformations (Wittig/HWE).
• For condensations that generate water, use molecular sieves or azeotropic removal to drive conversion.
• Dialdehydes may form hydrates; brief drying under high vacuum at ambient to mild temperatures can restore reactivity.

Reaction Conditions

Typical conditions by transformation (general literature guidance; adjust per substrate and scale):

• Imine formation (with primary amines/diamines):

  • Solvents: Toluene (Dean–Stark), ethanol, or DMSO/DMF.
  • Catalysis: Trace acid (acetic acid, p-toluenesulfonic acid) or molecular sieves (3Å/4Å) to remove water.
  • Temperature/time: RT–120°C (reflux, solvent-dependent), 2–24 h.
  • Notes: For COFs, use solvothermal conditions (e.g., mesitylene/dioxane/AcOH, 80–120°C) to promote crystallinity.

• Knoevenagel condensation (e.g., with malononitrile or cyanoacetates):

  • Solvents: Ethanol, acetonitrile, toluene, or DMF.
  • Bases: Piperidine, pyridine, ammonium acetate, or DBU (catalytic to stoichiometric).
  • Temperature/time: RT–80°C, 1–12 h.
  • Notes: Product often precipitates; isolated in moderate to high yields after filtration.

• Wittig/Horner–Wadsworth–Emmons olefination:

  • Solvents: Dry THF, CH2Cl2, toluene.
  • Bases: n-BuLi, NaH, or K2CO3 (HWE) under inert atmosphere.
  • Temperature/time: −78°C to RT (Wittig), 0–60°C (HWE), 1–6 h.
  • Notes: Ensure rigorously anhydrous conditions; aldehyde hydration reduces efficiency.

• Reductive amination (to diamines):

  • Solvents: MeOH, EtOH, or THF.
  • Reagents: NaBH3CN or NaBH(OAc)3 with anhydrous acid catalyst.
  • Temperature/time: 0–25°C, 2–18 h.

These are representative conditions reported broadly for dialdehydes and conjugated aromatic aldehydes; optimize for this specific substrate.

Safety and Handling

Item-specific GHS information (signal word, hazard statements, pictograms): Not specified for this item; refer to the SDS.

General laboratory safety guidance for heteroaromatic dialdehydes (informational, defer to SDS):

• Hazards: Aldehydes can be irritants and sensitizers; heteroaromatic compounds may cause skin/eye irritation. Avoid inhalation of dust and contact with skin/eyes.
• PPE: Lab coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile); handle powders in a fume hood to minimize dust exposure.
• Handling: Avoid prolonged exposure to air and moisture to limit hydrate formation or surface oxidation. Minimize light exposure for conjugated aromatics if photoreactivity is a concern.
• Incompatibilities: Strong oxidizers (risk of over-oxidation), strong bases (can trigger aldol/self-condensation or Cannizzaro-type side reactions in nonenolizable aldehydes), strong reducing agents (undesired reduction to alcohols). Prevent contact with acids/bases during storage.
• First aid (overview): Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Always follow your institution’s emergency procedures.
• Fire: Use CO2, dry chemical, or foam. Many heteroaromatics are combustible. Thermal decomposition may release sulfur- and nitrogen-containing irritants.

Always consult the product SDS for authoritative hazard classifications and response measures.

Solvent Selection

This compound is a rigid, π-conjugated, heteroaromatic dialdehyde. Solvent choice should balance solubility, reaction compatibility with aldehyde functionality, and downstream processing.

General/literature solvent behavior (not item-specific):

• Good solvents for dissolution and reactions: DMSO, DMF, NMP, DMAc, chlorobenzene, o-dichlorobenzene, chlorinated solvents (e.g., CH2Cl2) for small-scale work; hot acetonitrile or ethyl acetate may give moderate solubility.
• Limited solubility: Alcohols (may also participate in acetalization), ethers (THF, 2-MeTHF) at ambient temperature; solubility often improves with heat.
• Immiscibility: Essentially insoluble in water.

Selection tips by use-case:

• Imine/Schiff base formation and COF/polyimine synthesis: High-boiling polar aprotics (DMSO, NMP) or mixed solvent with toluene for azeotropic water removal.
• Knoevenagel-type condensations: Protic solvents (ethanol, isopropanol) or polar aprotics (DMF) with secondary amine bases; adjust to manage precipitation of products.
• Wittig/Horner–Wadsworth–Emmons: Dry THF, toluene, or CH2Cl2 for ylide/phosphonate chemistry; rigorously anhydrous conditions recommended.
• Film processing/spin coating (materials): Chlorobenzene or o-dichlorobenzene provide good wetting and slow evaporation for uniform films.

Comparison (general):

• DMSO/DMF: maximal solubility; harder workup.
• CH2Cl2/THF: convenient handling; may require heating or concentration to maintain dissolution.
• Chlorobenzene/o-DCB: device-relevant processing; higher boiling points enable slow-dry films.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per product data). Keep container tightly closed.
• Container atmosphere: Store under dry conditions. If available, use desiccant and minimize exposure to ambient humidity and light to limit hydrate formation or slow oxidation of aldehyde functions (general guidance).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solution preparation (general):
  • Start with dry, anhydrous solvent (e.g., DMSO, DMF, CH2Cl2, chlorobenzene) appropriate to your application.
  • Warm gently and agitate to assist dissolution; avoid prolonged heating with nucleophilic solvents that can react (alcohols, amines) unless intended.
  • For stock solutions, prepare under inert gas when possible and store in amber vials at 2–8°C or RT depending on solvent stability; use within days to weeks, checking for precipitation or discoloration.
• Stability notes (general): Aldehydes can slowly hydrate or polymerize; if reactivity appears diminished, dry under high vacuum at ambient to mild temperature before use.

Research Use Only: Not for human or animal therapeutic or diagnostic use.

Structure and Identity

This item is a conjugated heteroaromatic dialdehyde based on a 2,2′-bithiazole core with aldehyde groups at the 5,5′-positions.

• Product name: [2,2′-Bithiazole]-5,5′-dicarboxaldehyde
• CAS: 259542-09-1 (item-specific)
• Category: Materials science building block (conjugated heteroaromatic)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: 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.

Structural description (general/literature):

• Core: 2,2′-bithiazole (two thiazole rings C3N1S1 each, C2–C2′ linked) forming a planar, electron-deficient, π-conjugated scaffold.
• Substitution: Formyl (–CHO) groups at C5 and C5′.
• Functional groups: Two aldehydes (electrophilic), two thiazoles (N and S heteroatoms), extended aromatic system.
• 2D depiction in words: Two five-membered thiazole rings connected head-to-head at their 2-positions; each ring bears an aldehyde at the position para across the ring (5-position), resulting in –CHO termini on opposite ends of a linear, rigid, heteroaromatic framework.

Notes:

• The above structural features guide reactivity (e.g., imine formation, Wittig/Knoevenagel olefinations) and materials behavior (planarity, π-stacking). Item-specific identifiers beyond CAS are not provided in the current listing.

Synthetic Utility

Functional group ensemble and value (general/literature):

• Dual aldehydes: Two electrophilic sites enable symmetrical difunctionalization, step-growth polymerization, or macrocyclization. Compatible with imine formation, acetalization, oxime/hydrazone ligations, Wittig/HWE, and reductive amination.
• Bithiazole core: Electron-deficient, planar heteroaromatic that lowers LUMO energy when embedded in conjugated backbones, enhancing electron-transport character. The N and S heteroatoms can engage in coordination, hydrogen bonding, and S···X interactions that influence solid-state packing.

Strategic uses:

• Divergent synthesis: From the dialdehyde, access diacids (oxidation), diols (reduction), dinitriles (oxime → dehydration or via Knoevenagel with malononitrile), or distyryl derivatives (Wittig), each serving as handles for further cross-couplings or polymerizations.
• Materials tuning: Build A–A or A–D–A motifs for small-molecule acceptors; incorporate into donor–acceptor polymers via imine or vinylene linkages to tailor optical gaps and charge transport.
• Dynamic covalent chemistry: Reversible C=N bonds facilitate error-correction in framework assembly; post-synthetic locking via reduction to secondary amines provides robustness.

Practical notes:

• Control water content to favor desired pathways (e.g., anhydrous for Wittig; remove water for imines).
• Use mild bases/nucleophiles to avoid decomposition at the heteroaromatic core.

Target Specificity

Not applicable. This product is a small-molecule building block and does not possess biological target specificity (no antigen/epitope, clone, or isotype).