Production Method 1

5326-47-6

89979-12-4

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Dichloromethane ;  0 °C; overnight, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists

Li, Fu-Nan; Kim, Nam-Jung; Chang, Dong-Jo; Jang, Jaebong; Jang, Hannah; et al, Bioorganic & Medicinal Chemistry, 2009, 17(24), 8149-8160

5-chloro-2-methanesulfonamidobenzoic acid Raw materials

• 2-Amino-5-iodobenzoic acid

5-chloro-2-methanesulfonamidobenzoic acid Preparation Products

• 5-chloro-2-methanesulfonamidobenzoic acid (89979-12-4)

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Comprehensive Overview of 5-Chloro-2-methanesulfonamidobenzoic Acid (CAS No. 89979-12-4): Properties, Applications, and Research Insights

5-Chloro-2-methanesulfonamidobenzoic acid (CAS 89979-12-4) is a specialized organic compound with a molecular formula of C₈H₈ClNO₄S. This sulfonamide derivative has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural features, including a chloro-substituted benzene ring and a methanesulfonamide group. Its carboxylic acid functionality further enhances its reactivity, making it a versatile intermediate in synthetic chemistry.

In recent years, the demand for high-purity sulfonamide compounds like 5-chloro-2-methanesulfonamidobenzoic acid has surged, driven by their applications in drug discovery and material science. Researchers frequently search for "synthesis methods for sulfonamide derivatives" or "bioactivity of chloro-substituted benzoic acids," reflecting the compound's relevance in cutting-edge studies. Its molecular weight of 249.67 g/mol and crystalline solid form under standard conditions make it suitable for precise laboratory applications.

The compound's thermal stability (decomposing above 200°C) and moderate solubility in polar solvents (e.g., DMSO, methanol) are frequently discussed in forums about "optimizing sulfonamide reaction conditions." Analytical techniques such as HPLC and NMR spectroscopy are essential for characterizing its purity, a topic often queried as "CAS 89979-12-4 analytical standards." Notably, its logP value (~1.8) suggests balanced lipophilicity, crucial for pharmacokinetic studies.

Emerging trends highlight its potential in "targeted drug delivery systems" and "green chemistry approaches," with particular interest in its metal-chelating properties. Environmental scientists also explore its biodegradation pathways, addressing queries like "eco-friendly degradation of sulfonamides." Regulatory databases confirm its non-hazardous status under normal handling conditions, aligning with industrial safety standards.

From a commercial perspective, 5-chloro-2-methanesulfonamidobenzoic acid is listed in catalogs under "building blocks for heterocyclic synthesis" and "pharmaceutical intermediates." Patent literature reveals its utility in developing anti-inflammatory agents and enzyme inhibitors, answering frequent searches about "CAS 89979-12-4 patent applications." Current research focuses on its structure-activity relationships, particularly how the chloro and sulfonamide moieties influence biological interactions.

Quality control protocols emphasize chromatographic purity ≥98% and low heavy metal content, critical for compliance with "ICH Q3D guidelines." The compound's IR spectrum (characteristic peaks at 1700 cm^-1 for C=O and 1150 cm^-1 for S=O) serves as a fingerprint for identity verification, a technique often searched as "FTIR analysis of sulfonamides."

Future directions may explore its nanoparticle conjugates for enhanced bioavailability, responding to trends in "nanomedicine formulations." As synthetic methodologies evolve, catalytic C-H activation routes for its production could reduce environmental impact, addressing the popular query "green synthesis of benzoic acid derivatives."

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