121-53-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Sulfobenzoic acid is used as a precursor for the preparation of Proline derivatives, which are essential in the inhibition of β-Lactamase. This application is crucial in the development of antibiotics, as β-Lactamase is an enzyme that can break down the β-lactam ring in certain antibiotics, rendering them ineffective.
Used in Chemical Industry:
3-Sulfobenzoic acid serves as a derivative for the synthesis of surface-active agents. These agents, also known as surfactants, have various applications in the chemical industry, including detergents, emulsifiers, and wetting agents. The unique properties of 3-sulfobenzoic acid, such as its solubility in water and alcohol, make it a valuable component in the creation of these surface-active agents.

InChI:InChI=1/C7H6O5S/c8-7(9)5-2-1-3-6(4-5)13(10,11)12/h1-4H,(H,8,9)(H,10,11,12)

Upstream product

• 98-45-3 benzaldehyde-3-sulfonic acid 
• 98-07-7 Benzotrichlorid 
• 65-85-0 benzoic acid 
• 7446-11-9 sulfur trioxide 
• 7664-93-9 sulfuric acid 
• 98-87-3 benzylidene dichloride 
• 632-25-7 2-sulfobenzoic acid 
• 636-76-0 3-sulfamoylbenzoic acid 
• 64-17-5 ethanol 
• 109495-19-4 N,N'-bis(3-carboxy-phenyl)-triazene 
• 4025-64-3 3-Carboxybenzenesulfonyl chloride 
• 63914-81-8 chlorosulphonyl-benzoic acid 
• 7782-77-6 cis-nitrous acid 
• 7697-37-2 nitric acid 

Downstream Products

• 170169-31-0 3-methoxycarbonyl-benzenesulfonic acid 
• 121-91-5 isophthalic acid 
• 2136-81-4 3-chlorobenzotrichloride 
• 1227-49-2 3,3'-dithiobis-benzoic acid 
• 4052-92-0 3-chlorosulfonylbenzoyl dichloride 
• 4025-64-3 3-Carboxybenzenesulfonyl chloride 
• 89678-02-4 3-nitro-5-sulfo-benzoic acid 
• 58261-80-6 3-chlorocarbonyl-benzenesulfonic acid 
• 618-46-2 m-Chlorobenzoyl chloride 
• 80506-56-5 3-(2-Oxo-pentyloxysulfonyl)-benzoic acid 
• 99-06-9 3-Carboxyphenol 
• 65-85-0 benzoic acid 
• 535-80-8 3-chlorobenzoate 
• 89073-61-0 3-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid potassium salt 

Relevant academic research and scientific papers

ANTIBACTERIAL AGENTS

The present invention relates to antibacterial agents that are useful for sterilization, sanitation, antisepsis, and disinfection.

Process for preparing 3-sulfobenzoic acid and alkali metal salts thereof

Process for preparing 3-sulfobenzoic acid and alkali metal salts thereof is disclosed. The present invention relates to a process for preparing 3-sulfobenzoic acid and/or alkali metal salts thereof, which comprises mixing 3-(chlorosulfonyl)benzoic acid with water and a water-immiscible solvent in which 3-sulfobenzoic acid is insoluble or only sparingly soluble, removing water from the mixture by azeotropic distillation, cooling and, if desired, admixing the 3-sulfobenzoic acid formed with alkali metal hydroxide and/or a substance forming alkali metal hydroxide and again removing water by azeotropic distillation.

The positional reactivity order in the sulfur trioxide sulfonation of benzene and naphtalene derivatives containing an electron-withdrawing substituent

The reaction of sulfur trioxide with derivatives of benzene and naphthalene containing an electron-withdrawing substituent, viz.-SO3H, -SO2Ph, -NO2, -CHO, -COPh, -CO2H, and -CO2Me, in dichloromethane as solvent at ca. 22 deg C has been studied by analysis of the resulting mixtures of the sulfo derivatives with 1H-NMR.The initial sulfonation of the benzene derivatives yields the corresponding 3-sulfonic acid (3-S) and subsequently, with the exception of nitrobenzene and methyl benzoate, small amounts of 3,5-S2.Benzenesulfonic acid in addition undergoes sulfonylation giving 3,3'-di- and 3,5,3'-trisulfodiphenyl sulfone.Monosulfonation of naphtalene-1-S yields the 1,5-S2, 1,6-S2 and 1,7-S2 derivatives in a ratio of 71:20:9.On using a large excess of SO3, the eventual products are 1,3,5-S3, 1,3,6-S3 and 1,3,5,7-S4.Monosulfonation of naphthalene yields 5-S, 6-S, 7-S and 8-S in a 55:9:6:30 ratio, that of 1-benzoylnaphthalene 5-S, 6-S and 7-S in a ratio of 83:11:6, and 1-nitronaphtalene only the 5-S.The absence of peri sulfonation with 1-sulfo-, 1-benzoyl- and 1-nitronaphthalene is due to prohibitive steric hidrance. 1-Naphthoic acid and its methyl ester upon SO3 sulfonation and aqueous work-up both yield 5- and 8-sulfonaphthoic acid in a ratio of 65:35 and 77:21, respectively.The initially formed peri-substituted product is the intramolecular anhydride of 8-sulfo-1-naphthoic acid (5).All the 2-substituted naphthalenes yield 5-S and 8-S upon SO3 sulfonation of which the former sulfo isomer is far in excess.The positional reactivity orders for the SO3 sulfonation of the monosubstituted naphthalene derivatives are discussed in terms of the difference in reactivity of the α- and β-positions, and the steric and electronic effects of the deactivating substituent.

THE AQUEOUS PERIODATE OXIDATION OF AROMATIC AND ALIPHATIC CARBOXYLIC ACID DISULFIDES

The water-soluble carboxylic acid-functionalized aromatic disulfides, 3,3'-dithiodibenzoic acid and 5,5'-dithiodiisophthalic acid (5,5'-dithiodi(1,3-benzenedicarboxylic acid)) were prepared and their rates of periodate oxidation to the sulfonic acids were determined.The reaction is first order in each of the reactants which indicates that the slow step is the initial oxidative cleavage step.These aromatic disulfides are oxidized to the sulfonic acids 4-8 times more slowly than a typical aliphatic disulfide.In all cases, water solubility of the disulfide is of prime importance.The periodate oxidation of two aliphatic carboxylic acid analogs were also examined, however, in these cases, the reactions were multiphasic and intermediate thiosulfinates were observed by 1H NMR along with the sulfonic acids.Key words: Periodate; disulfide; thiosulfonate; sulfonic acid, carboxylic acid, ABTS.

Process for the preparation of 3-hydroxybenzoic acid

3-Hydroxybenzoic acid is obtained by reaction with an alkali metal hydroxide at a temperature of 220° to 450° C. and under a pressure of 1 to 120 bars, from a technical 3-sulphobenzoic acid mixture which contains sulphuric acid and/or sulphur trioxide and which contains at least 75% by weight of 3-sulphobenzoic acid, relative to the total organic constituents present, and not more than 35% by weight of sulphuric acid and/or SO3, relative to the total mass. For this purpose, this technical 3-sulphobenzoic acid mixture, if desired after dilution with an equal volume of water, is mixed with sufficient 50 to 100% strength by weight alkali metal hydroxide wherein the remaining 50 to 0% by weight consists essentially of water, for 2.5 to 8 mols of alkali metal hydroxide to be present per mol of 3-sulphobenzoic acid, after neutralization of the sulphuric acid and all the sulpho and carboxyl groups. In general, 10 to 45% by weight of water are present in the batch. The reaction mixture is acidified with a mineral acid to a pH value of less than 4, if appropriate after dilution with water, and the 3-hydroxybenzoic acid is isolated at temperatures within the range from -5° C. to +40° C.

A Method for the Separation of Benzoic Acids by Cation-excange Chromatography Using the AAA 881 Amino-acid Analyzer

The authors studied the separation of benzoic acid and its hydroxy derivatives by cation-excange chromatography.The AAA 881 amino-acid analyzer served to fractionate these substances.For this purpose, the amino-acid analyzer was connected with the Specord UV-VIS and the Uvicord II LKB 8300, respectively.M 82 resins, which are used in amino-acid analysis, were employed for separation.The substances were well separated from each other in a short time.Various buffer gradients were used in cation-excange chromatography.Sodium citrate buffers (pH-4.25 and 5.42) were em ployed in separating salicylic acid (o-hydroxybenzoic acid), m-hydroxybenzoic acid and p-hydroxybenzoic acid.A sodium borate buffer (pH=10.2) was utilized in fractionating benzoic acid on M 82 columns.Since dihydroxybenzoic acids may occur in the plant, animal and human organism as salicylic acid metabolites, these acids have been included in the present study. 2,3-Dihydroxybenzoic acid (o-pyrocatechuic acid) and 2,5-dihydroxybenzoic acid (gentisic acid) were separared from the starting material by means of MV 82 columns using a lithium citrate buffer (pH=3.1).The compounds under investigation were in part synthetized by the authors.Coupling of the AAA 881 amino-acid analyzer with the Specord UV-VIS and the Uvicord II LKB 8300 may also be used as a variant of the prefractionaction of animal or plant materials.