Chemical Identity and Structure

4-(Methanesulfonyl)benzoyl chloride (CAS number should be confirmed on the product CoA; review flag raised) is a para-disubstituted benzene derivative. The aromatic ring carries two strongly electron-withdrawing groups: the acyl chloride (–COCl) at the C-1 position and the methanesulfonyl group (–SO₂CH₃) at the C-4 position. This dual electron-withdrawing character renders the carbonyl carbon highly electrophilic, enhancing its reactivity toward nucleophilic acyl substitution compared with unactivated benzoyl chloride.

Its molecular formula is C₈H₇ClO₃S, with a molecular weight of 218.66 g/mol. The compound typically appears as a white to off-white solid or crystalline powder. The methanesulfonyl group also introduces aqueous solubility potential in downstream products, a desirable property in drug design contexts.

Synthesis Applications in Medicinal and Agrochemical Chemistry

The acyl chloride functionality of 4-(methanesulfonyl)benzoyl chloride makes it an efficient acylating agent for a broad range of nucleophiles:

• Amide bond formation: Reaction with primary or secondary amines yields substituted 4-(methanesulfonyl)benzamides. Such amide motifs are prevalent in bioactive molecules targeting enzymes and receptors.
• Ester synthesis: Treatment with alcohols or phenols in the presence of a base (e.g., triethylamine or pyridine) affords the corresponding esters, useful as prodrug linkers or in material-science applications.
• Sulfonamide-adjacent scaffolds: Because the methanesulfonyl group is metabolically robust, incorporation of this fragment into drug candidates can improve pharmacokinetic profiles including membrane permeability and metabolic stability.
• Agrochemical intermediates: The compound serves as a building block for herbicides and fungicides where sulfonyl-bearing aromatic systems confer target selectivity.

Reactions are typically conducted in anhydrous aprotic solvents such as dichloromethane, THF, or acetonitrile, with a tertiary amine base to scavenge the HCl generated during acylation.

Safe Handling, Storage, and Regulatory Considerations

As an acyl chloride, 4-(methanesulfonyl)benzoyl chloride is moisture-sensitive and reacts vigorously with water, alcohols, and amines upon uncontrolled exposure, releasing hydrogen chloride (HCl) gas. The following precautions are essential:

• Personal protective equipment (PPE): Lab coat, chemical-resistant gloves, and safety goggles must be worn at all times when handling this reagent. Use in a well-ventilated fume hood.
• Moisture exclusion: Reactions should be set up under inert gas (nitrogen or argon). Reagent vials should be resealed immediately after use and stored under inert atmosphere.
• Storage temperature: Maintain at 2–8 °C or as stated on the Certificate of Analysis (CoA). Keep away from incompatible materials including oxidizers, bases, and water.
• Waste disposal: Dispose of waste in accordance with local regulations for halogenated organic waste. Neutralize HCl-containing waste streams carefully before disposal.
• First aid: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air.

Always consult the Safety Data Sheet (SDS) supplied with the product for complete hazard information and emergency procedures.

Quality, Purity, and Procurement from Aladdin Scientific

Aladdin Scientific offers 4-(Methanesulfonyl)benzoyl chloride under SKU B725791. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity, appearance, and key spectroscopic data. Researchers should verify the CAS number, purity specification, and lot-specific data on the CoA before use to ensure suitability for their synthetic application.

For applications requiring stringent purity (e.g., pharmaceutical reference standards or GMP-adjacent research), procurement teams should request detailed analytical data including HPLC purity, NMR confirmation, and residual moisture content. Aladdin Scientific's technical support team can assist with custom packaging or bulk quantities for scale-up campaigns.

When comparing suppliers, key parameters to evaluate include: stated purity (%), moisture content, packaging size options, cold-chain shipping capability, and availability of an up-to-date SDS. Consistent lot-to-lot quality is critical for reproducible synthetic outcomes in process chemistry.