Chemical Structure and Key Properties

(5-Chlorothiophen-3-yl)methanol belongs to the thiophene family of five-membered sulfur-containing heterocycles. Its structure features a thiophene ring substituted with a chlorine atom at the 5-position and a hydroxymethyl (–CH₂OH) group at the 3-position. This combination of an electron-withdrawing aryl chloride and a nucleophilic primary alcohol on the same aromatic scaffold makes the compound bifunctionally reactive.

The thiophene ring confers aromatic stability and a degree of electron delocalization, while the chlorine substituent activates the ring toward nucleophilic aromatic substitution under appropriate conditions and also serves as a handle for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, or Stille couplings). The primary alcohol group can be oxidized to the corresponding aldehyde or carboxylic acid, converted to a leaving group (mesylate, tosylate, or halide), or directly employed in etherification and esterification reactions.

The molecular formula is C₅H₅ClOS with a molecular weight of approximately 148.61 g/mol. Physical data such as boiling point, melting point, refractive index, and density should be confirmed against the current Certificate of Analysis (CoA) or Safety Data Sheet (SDS) provided by Aladdin Scientific.

Synthesis and Applications in Research

(5-Chlorothiophen-3-yl)methanol is widely used as a synthetic intermediate and building block in multiple areas of chemical research:

• Medicinal Chemistry: Halogenated thiophene alcohols are established intermediates in the preparation of bioactive molecules. The chlorothiophene motif appears in pharmacophores targeting a range of biological pathways. The –CH₂OH group provides a convenient handle for elaboration into more complex drug candidates via oxidation, substitution, or coupling.
• Agrochemical Synthesis: Thiophene-containing scaffolds are found in several commercial herbicides, fungicides, and insecticides. (5-Chlorothiophen-3-yl)methanol can serve as a starting material for agrochemical lead optimization.
• Materials Science: Functionalized thiophenes are precursors to conducting polymers and organic semiconductors. Incorporation of halogen and hydroxyl substituents allows further polymerization or grafting chemistry.
• Cross-Coupling Chemistry: The C–Cl bond at the 5-position of the thiophene ring is amenable to palladium- or nickel-catalyzed cross-coupling, enabling C–C bond formation to introduce diverse aryl, alkenyl, or alkynyl substituents.

Researchers should optimize reaction conditions (catalyst loading, base, solvent, temperature) for each specific transformation, as reactivity can vary depending on the electronic and steric environment of the thiophene system.

Safe Handling, Storage, and Regulatory Considerations

As with all fine chemical reagents containing organohalogen and alcohol functionalities, appropriate precautions should be observed when handling (5-chlorothiophen-3-yl)methanol:

• Personal Protective Equipment (PPE): Wear nitrile gloves, safety goggles, and a lab coat. Where ventilation is limited, use a fume hood.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area, away from incompatible materials such as strong oxidizers and strong bases. Refer to the SDS for specific storage temperature recommendations.
• Waste Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic solvents and compounds.
• First Aid: In case of skin or eye contact, flush with copious amounts of water. Seek medical attention if irritation persists. Consult the full SDS for detailed first-aid measures.

The specific hazard classification (GHS pictograms, H-statements, P-statements) for this compound should be confirmed from the current SDS available through Aladdin Scientific's product page (SKU: C177319). Regulatory status may vary by jurisdiction.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies (5-chlorothiophen-3-yl)methanol under catalog number C177319. Each lot is supported by a Certificate of Analysis (CoA) documenting purity (typically determined by GC or HPLC), appearance, and key spectroscopic data. Researchers and procurement officers should request the CoA for the specific lot number received to verify compliance with experimental requirements.

For bulk quantities or custom specifications, contact Aladdin Scientific's sales team. Multiple pack sizes may be available to suit discovery-scale through scale-up needs. Pricing, lead times, and availability are subject to change; consult the current product listing on the Aladdin Scientific website for up-to-date information.

Storage conditions and shelf life should be confirmed from the product label and SDS. Proper inventory rotation and storage practices will maintain reagent integrity over time.