TCI N0017 1-Naphthalenesulfonyl Chloride, CAS 85-46-1, is a naphthalene derivative carrying a sulfonyl chloride group at the alpha position, a functional group that is highly reactive toward nucleophiles. In the laboratory, this compound serves as an important non-heterocyclic building block because it reacts readily with primary and secondary amines to form sulfonamides, and with alcohols and phenols to form sulfonate esters. These reactions are standard steps in organic synthesis, functional group protection, and analytical derivatization intended to make otherwise poorly detectable compounds easier to detect.
The property that makes this reagent a preferred choice is the high reactivity of the sulfonyl chloride group, which nevertheless remains controllable under ordinary reaction conditions, namely in aprotic solvents with the addition of an acid-scavenging base. The sulfonamide bond that is formed is very stable, so derivatization products withstand analytical conditions. The naphthalene framework provides strong ultraviolet absorption and fluorescent character in many of its derivatives, so attaching this group to a target molecule significantly increases detection sensitivity.
In Indonesian laboratories, this reagent fits the work of academic synthetic chemistry groups, analytical method development laboratories, and research and quality control units that need to prepare sulfonamide or sulfonate ester intermediates. It is typically used at bench scale in fume-hooded work, within reaction schemes that call for a reliable, well-characterized alpha-substituted naphthalene reagent supplied by TCI. As a consequence of its reactivity, the material is handled as a moisture-sensitive reagent throughout.
- Sulfonamide synthesis: reacts readily with primary and secondary amines to build stable sulfonamide bonds, a standard step in organic synthesis routes.
- Sulfonate ester preparation: reacts with alcohols and phenols to give sulfonate esters, providing a straightforward route to activated intermediates for further transformation.
- Functional group protection: the sulfonyl group masks reactive amine functionality during multi-step sequences, taking advantage of the stability of the sulfonamide bond formed.
- Analytical derivatization: converts poorly detectable compounds into naphthalene-tagged derivatives, since the naphthalene framework adds strong ultraviolet absorption for improved detection.
- Fluorescence-based detection work: many derivatives of this reagent are fluorescent, so tagging a target molecule significantly raises detection sensitivity in analytical methods.
| Brand | TCI |
|---|---|
| CAS number | 85-46-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in the standard TCI catalogue pack sizes; please confirm the packaging option required |
| Physical form | — |
| Storage | keep in a tightly closed container, protected from moisture |
- Chemical class: naphthalene derivative bearing a sulfonyl chloride group at the alpha position
Store the container tightly closed in a cool, dry place, protected from moisture and away from bases, alcohols, amines, and other nucleophilic materials, since the sulfonyl chloride group reacts readily with such substances. Use containers with well-sealed caps and return the material to storage promptly after weighing to limit exposure to atmospheric humidity. Handle in a fume hood using gloves, safety goggles, and a laboratory coat, and prepare reactions in aprotic solvents with an acid-scavenging base as the reaction conditions require. Clean spills and residues promptly, and follow the institutional chemical waste procedure for disposal.
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