4-Cyanobenzenesulfonyl Chloride TCI C1813

Chemical Identity

CAS No.: 49584-26-1
PubChem: CID 39497·SID 87558775
Formula: C7H4ClNO2S
Molecular weight: 201.62 g/mol
Purity: >98.0%(GC)(T)
Reference databases: ECHA

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 4-cyanobenzenesulfonyl chloride
SMILES: C1=CC(=CC=C1C#N)S(=O)(=O)Cl
InChIKey: DBMFYTQPPBBKHI-UHFFFAOYSA-N

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TCI C1813 4-Cyanobenzenesulfonyl Chloride (CAS 49584-26-1) is an aromatic sulfonyl chloride with a nitrile group in the para position. In the laboratory it works as a sulfonylation reagent: it converts amines into sulfonamides and alcohols into sulfonate esters. The literature reports the 4-cyanobenzenesulfonyl group as both a protecting group and an activating group for amines. It behaves much like the nosyl group because it can be removed under mild conditions with a thiol and a base. This makes it a useful alternative in multi-step synthesis.

Chemists choose this reagent because its electron-withdrawing nitrile group makes the sulfonyl chloride reactive. The same group makes the resulting sulfonamide acidic enough to alkylate, for example through a Mitsunobu reaction or alkylation with a weak base. The nitro group of the nosyl group is sensitive to some reductive conditions, while the cyano group tolerates more of them, which leaves more room when planning a synthetic route. The nitrile can also be converted into other groups later, and its distinctive infrared signal makes reactions easy to monitor.

In Indonesian laboratories, this reagent is useful to researchers in organic synthesis and medicinal chemistry who work with amines and peptides. University research groups, pharmaceutical development teams and contract synthesis laboratories can use it when they need an amine protecting group that comes off under mild conditions and survives reductive steps. It fits well in academic and industrial projects that build complex nitrogen-containing molecules over several synthetic steps.

Related TCI products

Sulfonamide formation from amines: the reactive sulfonyl chloride couples readily with primary and secondary amines, giving 4-cyanobenzenesulfonamides for further synthetic work.
Sulfonate ester preparation from alcohols: the reagent turns hydroxyl groups into sulfonate esters, which can serve as useful intermediates in organic synthesis sequences.
Amine protection and activation in multi-step synthesis: the 4-cyanobenzenesulfonyl group protects the amine and can later be removed under mild conditions with a thiol and a base, much like the nosyl group.
N-alkylation of sulfonamides through Mitsunobu or weak-base methods: the electron-withdrawing nitrile makes the sulfonamide NH acidic enough to alkylate efficiently under mild conditions.
Synthetic routes that include reductive steps: the cyano group withstands a number of reductive conditions better than the nitro group of nosyl reagents, so chemists have more freedom in route design.

Brand	TCI (product code C1813)
CAS number	49584-26-1
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes	as listed on the product page; contact AMI Scientific for available options
Physical form	see the TCI Certificate of Analysis and Safety Data Sheet
Storage	keep tightly closed and protected from moisture, following the manufacturer's recommendations

Sulfonyl chlorides as a class react with water and moisture, so store this reagent in its original, tightly sealed container in a cool, dry, well-ventilated place. Keep it away from water, bases, amines, alcohols and oxidizing agents. Recap the container immediately after each use, and consider an inert-atmosphere or desiccator environment if you open it often. Handle it inside a fume hood and wear chemical-resistant gloves, safety goggles and a lab coat. Avoid skin contact, eye contact and breathing in dust or vapours. Always read the TCI Safety Data Sheet for the specific hazard, storage and disposal instructions before use.

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