4-Chloro-5-sulfamoyl-salicylic Acid: Properties & Applications
4-Chloro-5-sulfamoyl-salicylic Acid: Properties & Applications
4-Chloro-5-sulfamoyl-salicylic Acid is a halogenated, sulfonamide-functionalized salicylic acid derivative that serves as a key building block in pharmaceutical synthesis and as a reference compound in analytical and medicinal chemistry research.
- Chemical Name
- 4-Chloro-5-sulfamoyl-salicylic Acid
- CAS Number
- To be confirmed — see review flags
- Molecular Formula
- C7H6ClNO5S
- Key Functional Groups
- Carboxylic acid, phenolic hydroxyl, sulfonamide, chloro substituent
- Product SKU
- C131980
- Primary Use
- Pharmaceutical intermediate and analytical reference standard
Chemical Identity and Structure
4-Chloro-5-sulfamoyl-salicylic Acid is an aromatic compound belonging to the salicylic acid family. Its structure features a benzene ring bearing four substituents: a hydroxyl group at position 1 (the phenolic OH characteristic of salicylates), a carboxylic acid at position 2, a chlorine atom at position 4, and a sulfamoyl group (–SO2NH2) at position 5. This combination of electron-withdrawing groups (–Cl, –COOH, –SO2NH2) on the aromatic ring confers distinctive acidity and reactivity compared with unsubstituted salicylic acid.
The molecular formula is C7H6ClNO5S, with a molecular weight of approximately 251.64 g/mol. The compound is typically a white to off-white crystalline solid. Researchers should consult the product certificate of analysis (CoA) for confirmed purity, melting point, and spectral data specific to lot C131980.
Pharmaceutical Relevance and Synthetic Utility
4-Chloro-5-sulfamoyl-salicylic Acid is widely recognized as a structural analogue and synthetic precursor relevant to the preparation of loop diuretics. Its core scaffold — a chloro-sulfonamido-substituted salicylate — is reminiscent of the pharmacophore present in furosemide (frusemide), a clinically important loop diuretic that acts by inhibiting the Na+/K+/2Cl− cotransporter (NKCC2) in the thick ascending limb of the loop of Henle. As such, this compound is used in medicinal chemistry research as a building block for the design and synthesis of novel diuretic candidates and related bioactive molecules.
Beyond diuretics, sulfonamide-bearing salicylate derivatives have attracted interest for their potential carbonic anhydrase inhibitory activity, anti-inflammatory properties, and utility as scaffolds for structure–activity relationship (SAR) studies. Researchers working on enzyme inhibition or fragment-based drug discovery may find this compound valuable as a starting material or as a reference comparator.
Handling, Storage, and Safety Considerations
As with all fine chemical reagents, 4-Chloro-5-sulfamoyl-salicylic Acid should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Work should be performed in a well-ventilated area or fume hood to minimise inhalation of dust. The compound contains a sulfonamide moiety; personnel with known sulfonamide sensitivities should exercise particular caution.
For storage, the compound should be kept in a tightly sealed container away from moisture, light, and incompatible materials such as strong oxidising agents and strong bases. Storage at room temperature under dry conditions is generally recommended for crystalline aromatic sulfonamides, but researchers should verify the specific storage conditions stated on the Aladdin product label and CoA for SKU C131980. Dispose of waste in accordance with local regulatory requirements for halogenated organic compounds.
Analytical Characterization and Quality Assurance
Characterization of 4-Chloro-5-sulfamoyl-salicylic Acid typically involves a combination of spectroscopic and chromatographic techniques. 1H NMR and 13C NMR spectroscopy confirm the aromatic substitution pattern and the presence of the sulfonamide NH2 protons. Infrared (IR) spectroscopy reveals characteristic absorptions for the carboxylic acid O–H stretch, the sulfonamide S=O stretches, and the C–Cl bond. High-performance liquid chromatography (HPLC) is routinely used to establish compound purity, while mass spectrometry (MS) provides molecular weight confirmation and fragmentation data consistent with the expected structure.
Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot of C131980, detailing purity (typically assessed by HPLC or titration), appearance, and key spectral identifiers. Customers are encouraged to request the CoA at the time of purchase to ensure the material meets the specifications required for their specific application.
Frequently asked questions
What is 4-Chloro-5-sulfamoyl-salicylic Acid used for in research?
It is primarily used as a pharmaceutical building block and synthetic intermediate, particularly in the preparation of loop diuretic analogues structurally related to furosemide. It is also employed as a reference compound in medicinal chemistry SAR studies and may be of interest for carbonic anhydrase inhibition research.
How should 4-Chloro-5-sulfamoyl-salicylic Acid (C131980) be stored?
The compound should be stored in a tightly closed container, protected from moisture and light, and kept away from strong oxidising agents and bases. Please refer to the Aladdin CoA and product label for the lot-specific recommended storage temperature and conditions.
Is 4-Chloro-5-sulfamoyl-salicylic Acid the same compound as a furosemide intermediate?
4-Chloro-5-sulfamoyl-salicylic Acid shares the core chloro-sulfonamido-salicylate scaffold of furosemide but is not identical to furosemide itself; furosemide additionally bears a furfurylamine substituent at the carboxylic acid. This compound can serve as an intermediate or analogue in furosemide-related synthetic pathways, but researchers should verify its role in their specific synthetic route.
What analytical methods are used to confirm the identity and purity of C131980?
Identity is typically confirmed by NMR spectroscopy (¹H and ¹³C), IR spectroscopy, and mass spectrometry. Purity is assessed by HPLC. Full details for each lot are provided in the Aladdin Certificate of Analysis supplied with the product.
References
- Aladdin Scientific product page: 4-Chloro-5-sulfamoyl-salicylic Acid, SKU C131980.
- Sørensen H et al. (general reference for sulfonamide salicylate chemistry and loop diuretic pharmacophores — placeholder; specific citation to be identified by editorial review).
- Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Reviews Drug Discovery, 2008.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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