1205-30-7

Basic information

• Product Name: 4-Chloro-5-sulphamoylbenzoic acid
• Synonyms: 3-(aminosulfonyl)-4-chloro-benzoicaci;4-chloro-3-sulfamoyl-benzoicaci;csba;4-CHLORO-3-SULFAMINEBENZOIC ACID;4-CHLORO-3-SULFAMOYLBENZOIC ACID;4-CHLORO-3-SULFONAMIDOBENZOIC ACID;4-CHLORO-3-SULPHAMOYLBENZOIC ACID;4-chloro-5-sulphamoylbenzoic acid
• CAS NO: 1205-30-7
• Molecular Formula: C₇H₆ClNO₄S
• Molecular Weight: 235.64
• EINECS: 214-882-1
• Product Categories: BenzoicAcidDerivative;Organic acids;API intermediates;Amines;Aromatics;Sulfur & Selenium Compounds;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 1205-30-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 256-258 °C(lit.)
• Boiling Point: 502.4 °C at 760 mmHg
• Flash Point: 257.6 °C
• Appearance: White powder
• Density: 1.649 g/cm³
• Vapor Pressure: 6.5E-11mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.44±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-5-sulphamoylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-5-sulphamoylbenzoic acid(1205-30-7)
• EPA Substance Registry System: 4-Chloro-5-sulphamoylbenzoic acid(1205-30-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DG5642600
• Hazardous Substances Data: 1205-30-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-5-sulphamoylbenzoic acid is used as an intermediate compound in the synthesis of various pharmaceuticals. Its role in the development of new drugs is crucial, as it contributes to the creation of molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, 4-Chloro-5-sulphamoylbenzoic acid is utilized as a key building block for the synthesis of complex organic molecules. Its unique structure allows chemists to explore various synthetic pathways and develop new compounds with diverse applications.
Used in Research and Development:
4-Chloro-5-sulphamoylbenzoic acid is also employed in research and development settings, where it aids scientists in understanding the structure-activity relationships of various drug candidates. By studying the properties and reactivity of 4-Chloro-5-sulphamoylbenzoic acid, researchers can gain insights into the design and optimization of new pharmaceutical agents.
Used in Quality Control and Analysis:
In the pharmaceutical industry, 4-Chloro-5-sulphamoylbenzoic acid is used for quality control and analysis purposes. Its presence as an impurity in clopamide tablets necessitates the development of accurate and reliable analytical methods to ensure the safety and efficacy of the final drug product. This includes the use of chromatographic-densitometric techniques to quantify the compound in tablet formulations.

InChI:InChI=1/C7H6ClNO4S/c8-5-2-1-4(7(10)11)3-6(5)14(9,12)13/h1-3H,(H,10,11)(H2,9,12,13)/p-1

Upstream product

• 1208-40-8 4-chloro-3-sulfamoylbenzoic acid methyl ester 
• 2494-79-3 4-chloro-3-(chlorosulfonyl)benzoic acid 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 89694-28-0 4-amino-3-sulfamoylbenzoic acid 
• 90196-34-2 2-chloro-5-(hydroxymethyl)benzenesulfonamide 
• 3279-81-0 2-chloro-5-formyl-benzenesulphonamide 
• 1211-77-4 3-sulfamoyl-4-chlorobenzoic acid ethyl ester 

Relevant articles and documents

Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors

The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isoforms) and also for hCA IV and IX (transmembrane isoforms) taking acetazolamide as standard drug. Most of these compounds exhibited excellent activity against all these isoforms. hCA I was inhibited with Kis in the range of 50.8–966.8 nM, while the glaucoma associated hCA II was inhibited with Kis in the range of 6.5–760.0 nM. Isoform hCA IV was inhibited with Kis in the range of 65.3–957.5 nM, whereas the tumor associated hypoxia induced hCA IX was inhibited with Kis in the range of 30.8–815.9 nM. The structure activity relationship study for the 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides against these isoforms was also inferred from the results.

An analysis of structural, spectroscopic signatures, reactivity and anti-bacterial study of synthetized 4-chloro-3-sulfamoylbenzoic acid

In the current study, 4-chloro-3-sulfamoylbenzoic acid (CSBA) has been synthetized from 4-chloro-3-sulfamoylbenzoate. The explicit structure of the titled compound was authenticated by single crystal X-ray diffraction, vibrational and electronic spectroscopic signatures. The unambiguous structure in solid state was confirmed by single crystal X-ray diffraction technique and Hirshfeld surface analysis. The X-ray analysis reflect that the titled compound was crystallized in monoclinic crystal system with P21/c space group a = 4.9576(3) ?, b = 6.0315(3) ?, c = 29.8923(16) ?, β = 92.628(3)°, volume = 892.89(8) ?3 and Z = 4. In the solid phase structure, the molecules were interconnected by O–H?O and N–H?O hydrogen bonds and C–H?O intermolecular interactions forming a two dimensional sheet. These contacts were further envisaged by 3D-hirshfeld surface studies (dnorm) and 2D-fingerprint plots; which suggested that the O?H(39.9percent) contact contributed the highest to the surface. The molecular, vibrational and electronic properties of titled compound investigated by using quantum chemical calculations at DFT/B3LYP/6-311 + G(d,p) level of theory. An analysis each fundamental vibrational mode was performed with the help of potential energy distribution (PED) using VEDA4 program. In addition, frontier orbital analysis, global reactivity parameters, natural bond order (NBO) analysis, non-linear optical (NLO) calculation and molecular electrostatic potential (MEP) analysis were performed by same method in same phase. Bond dissociation energies have been calculated for all single acyclic bonds in order to study autoxidation mechanism and degradation properties of the present investigated molecule. The titled compound displayed moderate anti-bacterial activity against gram-positive and gram-negative bacteria.

Design, synthesis and SAR study of novel sulfonylureas containing an alkenyl moiety

A series of sulfonylurea compounds was designed and synthesized via introducing an alkenyl moiety into the aryl-5 position and most title compounds exhibited enhanced antifungal activities and limited herbicidal activities compared with chlorsulfuron. Then, a CoMSIA calculation for antifungal activities was carried out to establish a 3D-QSAR model in which a cross-validated q2 of 0.585 and a correlation coefficient r2 of 0.989 were obtained. The derived model revealed that hydrophobic and electrostatic fields were the two most important factors for antifungal activity. Structure optimization was performed according to the CoMSIA model and compound 9z was found to be as potent as chlorothalonil in vitro against C. cornigerum, the pathogen of the wheat sharp eyespot disease. In order to study the fungicidal mechanism, 9z was successfully docked into yeast AHAS using a flexible molecular docking method and the resulting binding pattern was similar to that of chlorimuron-ethyl, indicating that the antifungal activity of compounds 9 was probably due to the inhibition of fungal AHAS.

SYNTHETIC ANALOGUES OF XANTHOHUMOL

The present invention relates to novel synthetic analogues of xanthohumol and the use thereof.

Antiviral medicaments

The invention is concerned with amino acid derivatives of the formula and salts of acidic compounds of formula I with bases, which are viral proteinase inhibitors useful as antiviral agents, especially for the treatment or prophylaxis of infections caused by Hepatitis C, Hepatitis G and human GB viruses.