Overview and Chemical Identity

3-Bromothiophene-2-carbonylchloride (SKU B701303) is a bifunctional heterocyclic reagent featuring two distinct reactive sites: an electrophilic acyl chloride carbonyl at the 2-position and an aryl bromide at the 3-position of the thiophene ring. This dual functionality makes it particularly valuable in multi-step synthesis where sequential or orthogonal transformations are required.

The molecular formula is C₅H₂BrClOS, and the compound belongs to the class of heteroaromatic acyl chlorides. The thiophene scaffold is widely exploited in medicinal chemistry and organic electronics due to its aromatic stability and tunable electronic properties.

Handling, Storage, and Safety

As an acyl chloride, 3-Bromothiophene-2-carbonylchloride is highly moisture-sensitive and reacts with atmospheric water to release hydrogen chloride (HCl) gas. All manipulations should be performed under an inert atmosphere (nitrogen or argon) using dry glassware and anhydrous solvents.

Recommended storage conditions are in a tightly sealed container, kept cool (2–8 °C is typical for acyl chlorides), away from moisture and incompatible materials such as bases, alcohols, and oxidizing agents. Consult the current Safety Data Sheet (SDS) for precise hazard classifications, GHS pictograms, and first-aid measures before use.

Personal protective equipment (PPE) including chemical-resistant gloves, a lab coat, and eye protection is mandatory. Work should be conducted in a well-ventilated fume hood to avoid inhalation of HCl vapors generated upon hydrolysis.

Synthetic Applications

The acyl chloride moiety of 3-Bromothiophene-2-carbonylchloride readily undergoes acylation reactions with nucleophiles such as amines (to form amides), alcohols (to form esters), and organometallic reagents. These transformations are foundational in constructing thiophene-containing pharmacophores and functional materials.

The aryl bromide at the 3-position serves as a handle for transition-metal-catalyzed cross-coupling reactions, including Suzuki-Miyaura, Negishi, Stille, and Buchwald-Hartwig couplings, enabling further diversification of the thiophene core after initial acylation. This orthogonal reactivity allows chemists to elaborate complex molecular architectures in a controlled, stepwise manner.

Thiophene-2-carbonyl derivatives are reported in the literature as intermediates in the synthesis of bioactive compounds, including kinase inhibitors, antimicrobial agents, and conjugated polymer monomers for organic photovoltaics.

Solvent Compatibility and Reaction Conditions

Anhydrous aprotic solvents are preferred for reactions involving 3-Bromothiophene-2-carbonylchloride. Commonly used solvents include dichloromethane (DCM), tetrahydrofuran (THF), toluene, and diethyl ether. Protic solvents (water, methanol, ethanol) should be strictly avoided unless the intended reaction is controlled hydrolysis or ester formation.

Acylation reactions typically require a base (e.g., triethylamine, pyridine, or DIPEA) to scavenge the HCl by-product and prevent acidic degradation of acid-sensitive substrates or products. Reaction temperatures vary by nucleophile: amine acylations often proceed at 0 °C to room temperature, while less reactive nucleophiles may require mild heating.

Quality, Purity, and Procurement

Aladdin Scientific supplies 3-Bromothiophene-2-carbonylchloride under SKU B701303. Researchers are advised to confirm the current purity specification, available pack sizes, and certificate of analysis (CoA) directly on the Aladdin Scientific product page or by contacting technical support, as these parameters may be updated.

For procurement inquiries, bulk pricing, or custom packaging, please contact Aladdin Scientific's sales team. Ensure compliance with your institution's chemical management policies and relevant import/export regulations when ordering halogenated acyl chloride reagents.