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Description
TCI D4222 2,6-Dichlorobenzenesulfonyl Chloride (CAS 6579-54-0) is a benzene-ring-based sulfonylation reagent that carries a sulfonyl chloride group together with two chlorine atoms at both ortho positions. As a non-heterocyclic building block, this compound is used to install aryl sulfonyl groups onto nucleophiles such as amines, alcohols, and phenols, producing sulfonamides or sulfonate esters. Reagents of this type matter in the laboratory because the sulfonyl group simultaneously acts as a protecting group, a good leaving group, and a structural motif that appears widely in bioactive compounds and agrochemical materials.
The distinguishing characteristic of this reagent is its 2,6-dichloro substitution pattern, which creates steric hindrance around the sulfonyl centre while at the same time lowering the electron density of the ring. This combination delivers useful selectivity: reactions tend to proceed in a more controlled manner toward less hindered nucleophiles, so researchers can differentiate, for example, primary amines from bulky secondary amines. The sulfonamides produced also carry a distinctive electronic and conformational character arising from the two chlorine atoms, which is frequently exploited in molecular design to tune proton acidity and shape.
In Indonesian laboratories, a reagent of this class is typically kept as part of a synthetic building block collection in university research groups, pharmaceutical and agrochemical R&D units, and analytical or method-development laboratories. It is generally drawn on for small-scale derivatisation and scaffold construction work, where a well-defined, brand-consistent reagent supplied by TCI supports reproducible results across repeated experiments and between different operators working on the same synthetic route.
Laboratory Applications
- Sulfonamide synthesis: reacts with primary and secondary amines to install the arylsulfonyl group, giving sulfonamide products whose electronic character is shaped by the two ortho chlorine atoms.
- Sulfonate ester preparation: converts alcohols and phenols into sulfonate esters, exploiting the sulfonyl group as a good leaving group for subsequent substitution chemistry in multi-step routes.
- Selective derivatisation of mixed nucleophiles: the 2,6-dichloro steric hindrance lets chemists favour less hindered nucleophiles, helping distinguish primary amines from bulky secondary amines in one pot.
- Amine protecting group chemistry: the arylsulfonyl moiety serves as a protecting group during synthesis, allowing other functional positions of a molecule to be modified without interference.
- Bioactive and agrochemical scaffold construction: supplies a sulfonyl motif commonly found in bioactive compounds and agrochemical materials, supporting medicinal and crop-protection discovery programmes.
Specifications
- Brand: TCI
- CAS number: 6579-54-0
- Chemical name: 2,6-Dichlorobenzenesulfonyl Chloride (catalogue code D4222)
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale catalogue packs; please confirm the size required when ordering
- Storage: keep in a tightly closed original container, protected from moisture, as described in the manufacturer's documentation
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from moisture, since sulfonyl chlorides are sensitive to water and humid air. Keep the material in its original manufacturer packaging or in a compatible tightly sealed container, clearly labelled and segregated from bases, alcohols, amines, and other reactive nucleophiles. Handle inside a fume hood using appropriate gloves, safety goggles, and a laboratory coat, and avoid inhalation of vapours or direct contact with skin and eyes. Transfer the reagent promptly and reseal the container to limit exposure to atmospheric moisture. Always consult the manufacturer's safety data sheet before use, and follow your institution's chemical waste procedures for residues and contaminated materials.
