TCI
2,3-Dihydrobenzofuran-5-sulfonyl Chloride TCI D3553
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Description
TCI D3553 2,3-Dihydrobenzofuran-5-sulfonyl Chloride is a sulfonyl chloride reagent built on a dihydrobenzofuran heterocyclic framework, and it serves as a reactive intermediate in organic synthesis. Its role in the laboratory is highly specific: it transfers a sulfonyl group together with its bicyclic scaffold onto another molecule through reaction with a nucleophile. In a single reaction step, chemists can attach the dihydrobenzofuran core to amines, alcohols, or phenols to form sulfonamides and sulfonate esters, motifs that appear across many families of active compounds designed through medicinal chemistry.
The main property that makes this reagent a preferred choice is the electrophilic reactivity of the sulfur atom in the sulfonyl chloride group, which is high yet remains controllable. Reactions with primary and secondary amines generally proceed from low temperature up to room temperature in the presence of an acid-scavenging base, so the products are clean and straightforward to purify. The 2,3-dihydrobenzofuran framework itself contributes a semi-rigid character, while its cyclic ether group improves relative solubility and provides hydrogen-bond acceptor interactions. This combination of clear-cut reactivity and a pharmacophore-relevant scaffold is what makes the reagent a practical building block.
In Indonesian laboratories, this reagent is typically used in synthetic organic and medicinal chemistry work at university research groups, institutional laboratories, and industrial R&D units that prepare compound libraries or intermediates. It is normally handled on a small preparative scale in a fume hood, using dry solvents and an acid-scavenging base, then worked up and purified before characterization. Because it is a moisture-sensitive reagent, it is usually ordered in small pack sizes matched to the planned reaction sequence.
Laboratory Applications
- Sulfonamide synthesis — reaction with primary or secondary amines in the presence of an acid-scavenging base installs the dihydrobenzofuran sulfonamide motif in a single, easily purified step.
- Sulfonate ester preparation — alcohols and phenols react with the sulfonyl chloride group to give sulfonate esters that carry the intact bicyclic heterocyclic scaffold.
- Medicinal chemistry building block work — the semi-rigid dihydrobenzofuran core and its hydrogen-bond accepting cyclic ether make it useful for constructing pharmacophore-relevant fragments.
- Compound library and analogue synthesis — its controllable electrophilic reactivity toward different nucleophiles allows parallel preparation of related sulfonamide and sulfonate ester analogues.
- Derivatization of nucleophilic substrates — chemists use it to introduce a defined sulfonyl group onto amine, alcohol, or phenol functionalities during multi-step synthetic routes.
Specifications
- Brand: TCI
- CAS Number: 115010-11-2
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Chemical name: 2,3-Dihydrobenzofuran-5-sulfonyl Chloride
- Catalogue code: D3553
- Pack sizes: available in TCI research-scale packaging; please confirm the currently offered pack size when ordering
- Storage: keep in a tightly closed container, protected from moisture
Handling and Storage
Store the reagent in its original tightly closed container, protected from moisture and away from water, alcohols, amines, and other nucleophilic materials, since sulfonyl chlorides are readily hydrolysed by atmospheric humidity. Glass containers with chemically resistant closures are suitable, and the container should be allowed to reach room temperature before opening to avoid condensation on the contents. Handle and weigh the material inside a fume hood while wearing safety glasses, chemically resistant gloves, and a laboratory coat, because sulfonyl chlorides are corrosive and irritating and can release acidic by-products on contact with water. Use dry glassware and dry solvents for transfers, close the container immediately after use, and follow the manufacturer's Safety Data Sheet along with local laboratory waste procedures for disposal of residues and quenched reaction mixtures.
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