20532-05-2

Basic information

• Product Name: 4-METHYL-3-SULFAMOYLBENZOIC ACID
• Synonyms: 3-(AMINOSULFONYL)-4-METHYLBENZOIC ACID;4-METHYL-3-SULFAMOYLBENZOIC ACID
• CAS NO: 20532-05-2
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• Mol File: 20532-05-2.mol

Chemical Properties

• Melting Point: 267-269 °C(Solv: water (7732-18-5))
• Boiling Point: 487°C at 760 mmHg
• Flash Point: 248.3°C
• Appearance: /
• Density: 1.462g/cm³
• Vapor Pressure: 2.67E-10mmHg at 25°C
• Refractive Index: 1.596
• PKA: 3.84±0.10(Predicted)
• CAS DataBase Reference: 4-METHYL-3-SULFAMOYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-3-SULFAMOYLBENZOIC ACID(20532-05-2)
• EPA Substance Registry System: 4-METHYL-3-SULFAMOYLBENZOIC ACID(20532-05-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Hazardous Substances Data: 20532-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-3-SULFAMOYLBENZOIC ACID is used as a key component in the synthesis of sulfonamide-based antibiotics and antidiabetic medications. Its sulfonamide group contributes to the therapeutic properties of these drugs, making it an essential part of their chemical structure.
Used in Organic Chemistry:
4-METHYL-3-SULFAMOYLBENZOIC ACID serves as a reagent in organic chemistry reactions, particularly in the formation of amide and peptide bonds. Its strong hydrogen bonding capabilities facilitate these reactions, making it a valuable tool in the synthesis of various organic compounds.

InChI:InChI=1/C8H9NO4S/c1-5-2-3-6(8(10)11)4-7(5)14(9,12)13/h2-4H,1H3,(H,10,11)(H2,9,12,13)

Upstream product

• 2548-29-0 3-(chlorosulfonyl)-4-methylbenzoic acid 
• 99-94-5 p-Toluic acid 

Downstream Products

• 99-94-5 p-Toluic acid 
• 91013-59-1 3-Sulfamoyl-p-tolylsaeureethylester 
• 1189543-85-8 5-(4-methoxy-benzoyl)-2-methyl-benzenesulfonamide 
• 51119-87-0 2-methyl-5-vinylbenzenesulfonamide 
• 1093988-26-1 5-[5-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1,3,4-oxadiazol-2-yl]-2-methylbenzenesulfonamide 
• 1189545-95-6 N-methoxy-4,N-dimethyl-3-sulfamoyl-benzamide 
• 80998-66-9 2-sulfamoylterephthalic acid 
• 59815-25-7 4'-Methyl-3'-sulfamoyl-2-chloroacetophenone 
• 59815-24-6 4'-methyl-3'-sulfamoyl-diazoacetophenone 
• 90610-75-6 3-Sulfamoyl-p-tolylsaeuremethylester 
• 636-94-2 2-hydroxyterephthalic acid 
• 59815-23-5 4-methyl-3-sulfamoyl-benzoyl chloride 
• 956117-81-0 C₉H₁₀BrNO₄S 

Relevant articles and documents

Design and synthesis of benzenesulfonamide-linked imidazo[2,1-b][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors

A novel series of imidazothiadiazole-linked benzenesulfonamide derivatives (5a–t) was synthesized and subjected for screening against the four physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms: hCA I, II, VA, and IX. The compounds selectively inhibited hCA I and II over hCA VA and IX. Furthermore, among the two cytosolic isoforms, hCA II was more effectively inhibited as compared with hCA I. The most active compounds were 5o with Ki = 0.246 μM and 5p with Ki = 0.376 μM against hCA II, whereas compound 5f showed good inhibition against both hCA I and II with Ki = 0.493 and 0.4 μM, respectively. This class of underexplored sulfonamides may be used to design isoform-selective CA inhibitors targeting enzymes of medicinal chemistry interest.

3-Functionalised benzenesulphonamide based 1,3,4-oxadiazoles as selective carbonic anhydrase XIII inhibitors: Design, synthesis and biological evaluation

A new series of benzenesulphonamide linked-1,3,4-oxadiazole hybrids (6a–s) has been synthesized and tested for their carbonic anhydrase inhibition against human (h) carbonic anhydrase (CA) isoforms hCA I, II, IX, and XIII. Fluorescence properties of some of the synthesized molecules were studied. Most of the molecules exhibited significant inhibitory power, comparable or better than the standard drug acetazolamide (AAZ) on hCA XIII. Out of 19 tested molecules, compound 6e (75.8 nM) was 3 times more potent than AAZ (250.0 nM) against hCA I, whereas compound 6e (15.4 nM), 6g (16.2 nM), 6h (16.4 nM) and 6i (17.0 nM) were found to be more potent than AAZ (17.0 nM) against isoform hCA XIII. It is anticipated that these compounds could be taken as the potential leads for the development of selective hCA XIII isoform inhibitors with improved potency.

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.

ARYLSULFONAMIDE-BASED MATRIX METALLOPROTEASE INHIBITORS

The present invention provides a compound of formula (I):said compound is inhibitor of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP-13, and thus can be employed for the treatment of a disorder or disease characterized by abnormal activity of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP- 13. Accordingly, the compound of formula (I) can be used in treatment of disorders or diseases mediated by MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12, and/or MMP- 13. Finally, the present invention also provides a pharmaceutical composition.

INTEGRASE INHIBITORS 3

The present invention provides a method of treatment or prophylaxis of a viral infection in a subject comprising administering to said subject an effective amount of a compound of formula (I) or a pharmaceutically acceptable derivative, salt or prodrug thereof. Compounds of formula (I) are also provided.

Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury

A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H+exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests.

Agricultural sulfonamides

This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted by two carboxyl radicals. The compounds have utility as herbicides.