Chemical Identity and Properties

3-(Cyclopropylsulfamoyl)benzoic acid (Aladdin SKU: C187123) is an aromatic compound featuring a benzoic acid core with a sulfonamide group at the meta position, where the sulfonamide nitrogen carries a cyclopropyl substituent. This dual-functionality — a free carboxylic acid and a secondary sulfonamide — makes it a highly reactive and versatile building block for multi-step organic synthesis.

The sulfonamide moiety (–SO₂NH–) imparts moderate acidity to the N–H proton and allows participation in hydrogen-bonding networks, which is pharmacologically advantageous for target binding in drug candidates. The cyclopropyl group contributes conformational rigidity and metabolic stability, properties that are frequently exploited in lead optimization campaigns. The carboxylic acid group provides a handle for amide coupling, esterification, and other condensation reactions.

Note: Specific physicochemical data (exact melting point, solubility values, pKa) are not provided in the current source material. Researchers should consult the product specification sheet supplied with SKU C187123 or perform in-house characterization.

Safe Handling and Storage Protocol

Personal Protective Equipment (PPE): When handling 3-(Cyclopropylsulfamoyl)benzoic acid, wear appropriate PPE including chemical-resistant gloves (nitrile recommended), a laboratory coat, and safety goggles. Where dust generation is possible during weighing, use a fume hood or respiratory protection.

Storage Conditions: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area. Keep away from strong oxidizing agents, strong bases, and strong reducing agents, which may react with the carboxylic acid or sulfonamide functional groups. Avoid exposure to moisture and prolonged exposure to light.

Waste Disposal: Dispose of waste material in accordance with local, regional, and national regulations for chemical waste. Do not pour down the drain without consulting applicable regulations.

First Aid: In case of skin contact, wash thoroughly with soap and water. In case of eye contact, rinse immediately with copious amounts of water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air. Consult the Safety Data Sheet (SDS) for complete hazard information.

Note: A full SDS for SKU C187123 should be obtained from Aladdin Scientific prior to use. All specific hazard classifications should be confirmed therein.

Applications in Research and Synthesis

Medicinal Chemistry and Drug Discovery: The dual functional groups of 3-(Cyclopropylsulfamoyl)benzoic acid make it an important building block in pharmaceutical research. The carboxylic acid can be coupled with amines to form amide bonds using standard reagents (e.g., HATU, EDC/HOBt, or HBTU), enabling rapid construction of compound libraries for biological screening.

Scaffold Decoration: The secondary sulfonamide N–H can be alkylated, acylated, or used as a hydrogen-bond donor in structure–activity relationship (SAR) studies. The cyclopropyl group on the sulfonamide nitrogen is a well-established bioisostere and is incorporated into drug candidates to improve metabolic stability and modulate physicochemical properties such as lipophilicity and aqueous solubility.

Fragment-Based and Lead Optimization: Compounds containing both sulfonamide and carboxylic acid pharmacophores are common in fragment-based drug discovery (FBDD). This compound may serve as a fragment or an intermediate in the synthesis of more complex drug-like molecules targeting enzyme active sites or protein–protein interaction interfaces.

Materials and Coordination Chemistry: Benzoic acid derivatives with additional coordinating groups have also found use in the design of metal-organic frameworks (MOFs) and coordination polymers, though the primary utility of this compound remains in medicinal chemistry.

Recommended Experimental Protocol for Amide Coupling

The following general protocol describes the use of 3-(Cyclopropylsulfamoyl)benzoic acid as a carboxylic acid coupling partner in amide bond formation. This is a guideline only; researchers should optimize conditions for their specific substrates.

1. Dissolve 1.0 equivalent of 3-(Cyclopropylsulfamoyl)benzoic acid in anhydrous DMF (or DCM) at a concentration of 0.1–0.5 M.
2. Add 1.1–1.2 equivalents of a coupling reagent (e.g., HATU or EDC·HCl) followed by 1.5–2.0 equivalents of a base (e.g., DIPEA or triethylamine). Stir for 5–10 minutes at room temperature to activate the carboxylic acid.
3. Add 1.0–1.1 equivalents of the desired amine coupling partner and continue stirring at room temperature (or as dictated by substrate reactivity) for 1–16 hours.
4. Monitor reaction progress by TLC or LCMS.
5. Work up by diluting with ethyl acetate, washing with aqueous citric acid (to remove base and unreacted amine), saturated NaHCO₃ (to remove coupling reagent by-products), and brine. Dry over Na₂SO₄, filter, and concentrate.
6. Purify by column chromatography (silica gel) or preparative HPLC as appropriate.

Note: The sulfonamide N–H may require protection depending on downstream transformations. Consult literature on sulfonamide protection strategies if competing reactivity is observed.

Quality, Purity, and Specification Considerations

When ordering 3-(Cyclopropylsulfamoyl)benzoic acid (SKU C187123) from Aladdin Scientific, researchers should request and review the Certificate of Analysis (CoA) supplied with each lot. Key quality parameters to verify include:

• Purity: Confirm purity by HPLC or NMR as indicated on the CoA. For demanding synthetic applications, purity ≥95% is generally recommended.
• Identity Confirmation: ¹H NMR and/or HRMS data on the CoA should confirm the structural identity of the compound, including the integrity of the cyclopropyl group, the sulfonamide N–H, and the carboxylic acid.
• Appearance: The compound is expected to be a solid (powder or crystalline material). Significant discoloration or clumping may indicate degradation and the lot should be assessed before use.
• Lot-to-Lot Consistency: For reproducible biological assay results, request the same or comparable lot when re-ordering.

Contact Aladdin Scientific customer support for technical inquiries about purity grades, custom quantities, or bulk orders of SKU C187123.