Chemical Structure and Key Properties

4-Chloro-N-cyclopropylbenzenesulfonamide (SKU: C699218) belongs to the sulfonamide class of organic compounds. Its structure consists of a para-chlorinated benzene ring bearing a sulfonyl group (–SO₂–) that bridges to a cyclopropylamine nitrogen, forming the characteristic sulfonamide linkage (–SO₂NH–).

The para-chloro substituent on the phenyl ring modulates the electron density of the sulfonyl moiety, enhancing electrophilicity at sulfur and influencing the acidity of the N–H bond. The strained cyclopropyl ring introduces unique conformational rigidity and bioisosteric properties relative to larger alkyl or aryl groups, attributes that are frequently exploited in pharmaceutical design.

Key physicochemical features include moderate lipophilicity, hydrogen-bond donor capacity at the sulfonamide nitrogen, and two hydrogen-bond acceptor oxygens on the sulfonyl group—a profile compatible with drug-likeness criteria.

Synthesis and Handling

Sulfonamides of this type are classically prepared by reacting a sulfonyl chloride—in this case 4-chlorobenzenesulfonyl chloride—with cyclopropylamine in the presence of a base such as triethylamine or pyridine, which neutralises the HCl generated. The reaction is typically carried out in an aprotic solvent (e.g., dichloromethane or tetrahydrofuran) at or below room temperature to suppress side reactions.

When working with this reagent, standard laboratory precautions apply: use appropriate personal protective equipment including nitrile gloves, safety glasses and a lab coat. Perform reactions involving sulfonyl chloride precursors in a well-ventilated fume hood. Consult the Safety Data Sheet (SDS) for specific hazard and first-aid information before use.

The compound should be stored in a tightly sealed container in a cool, dry environment away from light and moisture to maintain long-term stability.

Research and Medicinal Chemistry Applications

Sulfonamide motifs are among the most prevalent pharmacophores in approved pharmaceuticals, appearing in antibacterials, diuretics, antidiabetics, and kinase inhibitors. 4-Chloro-N-cyclopropylbenzenesulfonamide serves as a versatile synthetic building block enabling researchers to introduce the para-chlorophenylsulfonyl and cyclopropyl pharmacophoric elements into target molecules.

The cyclopropyl group is a recognised bioisostere for vinyl groups and can improve metabolic stability relative to open-chain analogues. Combined with the electron-withdrawing chloro substituent, this compound offers a useful handle for structure–activity relationship (SAR) studies in lead optimisation campaigns.

Beyond medicinal chemistry, sulfonamide building blocks are employed in agrochemical research, supramolecular chemistry (as hydrogen-bond donors in crystal engineering), and as chiral auxiliaries or ligand components in asymmetric synthesis.

Quality and Procurement

Aladdin Scientific supplies 4-Chloro-N-cyclopropylbenzenesulfonamide (SKU: C699218) as a research-grade reagent. Each lot is subject to quality control analysis to confirm identity and purity before release. Researchers and procurement teams can request certificates of analysis (CoA) and Safety Data Sheets directly through the Aladdin Scientific website or customer service team.

For bulk quantities, custom packaging, or technical enquiries regarding this compound, please contact Aladdin Scientific sales support. Competitive pricing and reliable supply are maintained to support ongoing research programmes.