Chemical Identity and Structure

5-(Trifluoromethyl)thiophene-2-carbaldehyde is an aromatic heterocyclic compound featuring a thiophene ring substituted at the 2-position with an aldehyde group and at the 5-position with a trifluoromethyl (–CF3) group. The combination of the electron-withdrawing –CF3 moiety and the reactive aldehyde on a sulfur-containing aromatic system produces a highly polarised, electrophilic molecule. The molecular formula is C₆H₃F₃OS, with a molecular weight of approximately 180.15 g/mol. Its planar thiophene core facilitates π-stacking interactions, making it attractive for drug-discovery programs targeting protein binding sites.

The –CF3 group confers increased lipophilicity, metabolic stability, and membrane permeability to derived structures—properties highly valued in pharmaceutical lead optimisation. The aldehyde functionality provides a convenient handle for condensation reactions, reductive aminations, and Wittig-type olefinations.

Applications in Synthetic and Medicinal Chemistry

5-(Trifluoromethyl)thiophene-2-carbaldehyde is primarily used as an electrophilic building block in multi-step organic synthesis. Its aldehyde group participates readily in:

• Reductive amination – coupling with primary or secondary amines in the presence of a reducing agent (e.g., NaBH3CN or NaBH(OAc)3) to yield fluorinated thienyl amines.
• Knoevenagel condensation – reaction with active methylene compounds to give α,β-unsaturated derivatives useful as fluorophore precursors or bioactive scaffolds.
• Schiff base formation – condensation with amines to produce imines for use as ligands or pharmacophores.
• Wittig / HWE olefination – conversion of the aldehyde to vinyl derivatives for further elaboration.

In medicinal chemistry, the trifluoromethylthiophene motif appears in several classes of enzyme inhibitors and receptor modulators, where the –CF3 group improves binding affinity and oral bioavailability of lead compounds. Researchers in agrochemical development also employ fluorinated thiophene aldehydes as precursors to herbicidal and fungicidal agents.

Handling, Storage, and Stability

As with most aromatic aldehydes, 5-(Trifluoromethyl)thiophene-2-carbaldehyde should be handled with standard laboratory precautions:

• Personal protection: Wear chemical-resistant gloves, lab coat, and safety glasses. Work in a well-ventilated fume hood to avoid inhalation of vapours.
• Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the Certificate of Analysis), dry location, protected from light and moisture. Prolonged exposure to air can lead to slow oxidation of the aldehyde to the corresponding carboxylic acid.
• Stability: The compound is moisture-sensitive due to potential hemiacetal or acetal formation. Desiccant packing is recommended for long-term storage.
• Incompatibilities: Avoid contact with strong oxidising agents, strong bases, and reactive nucleophiles that could prematurely consume the aldehyde functionality.

Always consult the product's Safety Data Sheet (SDS) and Certificate of Analysis (CoA) provided by Aladdin Scientific for lot-specific purity data and confirmed storage conditions before use.

Ordering and Specifications

5-(Trifluoromethyl)thiophene-2-carbaldehyde is available from Aladdin Scientific under SKU T1034726. When placing an order, researchers and procurement specialists should note:

• Purity: Confirm the purity grade (typically ≥95% or ≥97% by GC or HPLC) on the current lot CoA. Contact Aladdin Scientific for lot-specific analytical data if required for regulated research.
• Pack sizes: Multiple pack sizes may be available. Contact Aladdin Scientific sales for bulk or custom quantities.
• Lead time: Standard catalogue items are typically dispatched promptly; confirm availability and lead time with Aladdin Scientific customer service for large quantities.
• Documentation: SDS, CoA, and structural confirmation (NMR, MS) are available upon request.

For international orders, shipping regulations for chemical reagents apply. Aladdin Scientific handles customs documentation and complies with applicable export regulations.

Quality, Purity, and Analytical Characterisation

Research-grade 5-(Trifluoromethyl)thiophene-2-carbaldehyde from Aladdin Scientific is characterised by standard analytical techniques to ensure suitability for synthetic and biological applications:

• GC or HPLC purity: Lot-specific purity is reported on the CoA. Typical research-grade material is ≥95% pure (verify on current CoA).
• NMR (¹H and ¹³C): Confirms correct regiochemistry of –CHO at C-2 and –CF3 at C-5 of the thiophene ring. The aldehyde proton typically appears near δ 9.9–10.0 ppm (CDCl3).
• ¹⁹F NMR: The –CF3 group gives a characteristic singlet; this provides rapid confirmation of the trifluoromethyl substituent.
• Mass spectrometry: ESI-MS or EI-MS confirms the molecular ion at m/z 180.15.
• IR spectroscopy: A strong carbonyl stretch near 1680 cm⁻¹ (conjugated aldehyde on heteroaromatic ring) confirms the aldehyde functionality.

Researchers requiring custom purity grades (e.g., ≥98%) or additional analytical documentation should contact Aladdin Scientific directly.