Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6O3S |
Molecular Weight | 158.175 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(=O)(=O)C1=CC=CC=C1
InChI
InChIKey=SRSXLGNVWSONIS-UHFFFAOYSA-N
InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
Molecular Formula | C6H6O3S |
Molecular Weight | 158.175 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26529301 | https://www.ncbi.nlm.nih.gov/pubmed/28391947 | https://www.ncbi.nlm.nih.gov/pubmed/926196
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26529301 | https://www.ncbi.nlm.nih.gov/pubmed/28391947 | https://www.ncbi.nlm.nih.gov/pubmed/926196
Benzenesulfonic acid (conjugate base benzenesulfonate) is the simplest aromatic sulfonic acid, that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. Benzenesulfonic acid was first obtained, together with diphenyl sulfone, by E. MITSCHERLICH in 1834 by heating benzene with fuming sulfuric acid. The industrially important reaction of benzenesulfonic acid with alkali hydroxide to form phenol (alkali fusion) was developed by A. WURTZ and A. KEKUL_e in 1867 and by P. O. DEGENER in 1878. Until the early 1960s benzenesulfonic acid was used chiefly in the manufacture of phenol. Benzenesulfonic acid has the characteristic reactions of a strong aromatic sulfonic acid. Acid hydrolysis at 175 C splits it into benzene and sulfuric acid. Additional sulfonation with fuming sulfuric acid gives 1,3-benzenedisulfonic acid, which reacts further to 1,3,5-benzenetrisulfonic acid, and also diphenyl sulfone disulfonic acid. Benzenesulfonic acid is used as an acid catalyst. The sodium salt is used to standardize dyes. A variety of pharmaceutical drugs are prepared as benzenesulfonate salts and are known as besilates (INN) or besylates (USAN).
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Fenton degradation of organic compounds promoted by dyes under visible irradiation. | 2005 Aug 1 |
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Dihydroxy-2,5 benzenesulphonate (dobesilate) elicits growth arrest and apoptosis in glioma cells. | 2005 Dec |
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Ab initio and DFT study of the geometric structures and static dipole (hyper)polarizabilities of aromatic anions. | 2005 Nov 17 |
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Raman spectroscopic study of hydrogen bonding in benzenesulfonic acid/acrylonitrile solutions. | 2005 Oct |
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Anaerobic digestion of linear alkyl benzene sulfonates: biodegradation kinetics and metabolite analysis. | 2005 Sep |
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Ferromagnetic coupling promoted by kappa3N:kappa2N bridging system. | 2006 Aug 7 |
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Inhibition of (Na(+)/K(+))-ATPase by Cibacron Blue 3G-A and its analogues. | 2006 Dec |
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Permeation flux of organic molecules through silica-surfactant nanochannels in a porous alumina membrane. | 2006 Dec |
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Hierarchical ionic self-assembly of rod-comb block copolypeptide-surfactant complexes. | 2006 Dec |
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Carbon-fiber microelectrodes modified with 4-sulfobenzene have increased sensitivity and selectivity for catecholamines. | 2006 Feb 28 |
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Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid. | 2006 Feb 3 |
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Formation of drug-arylsulfonate complexes inside liposomes: a novel approach to improve drug retention. | 2006 Jan 10 |
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Enrichment of N-terminal sulfonated peptides by a water-soluble fullerene derivative and its applications to highly efficient proteomics. | 2006 Jan 18 |
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The suramin analog 4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetra-kis-benzenesulfonic acid (NF110) potently blocks P2X3 receptors: subtype selectivity is determined by location of sulfonic acid groups. | 2006 Jun |
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Low level determination of p-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry. | 2006 Jun 30 |
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Acid-base equilibria in 5,10,15,20-tetrakis(4-sulfonatophenyl)chlorin: Role of conformational flexibility. | 2006 Mar 16 |
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Iron porphyrin-cyclodextrin supramolecular complex as a functional model of myoglobin in aqueous solution. | 2006 May 29 |
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Inorganic asymmetric synthesis: asymmetric synthesis of a two-bladed propeller, octahedral metal complex. | 2006 Oct 16 |
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A scalable machine-learning approach to recognize chemical names within large text databases. | 2006 Sep 6 |
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Study of biodegradation products from azo dyes in fungal degradation by capillary electrophoresis/electrospray mass spectrometry. | 2007 Aug 3 |
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The behaviour of linear alkyl benzene sulphonate under direct discharge conditions in Vientiane, Lao PDR. | 2007 Dec |
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Detection of hypoxia-related proteins in medaka (Oryzias latipes) brain tissue by difference gel electrophoresis and de novo sequencing of 4-sulfophenyl isothiocyanate-derivatized peptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2007 Feb |
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Lateral phase separation gives multiple lamellar phases in a "binary" surfactant/water system: the phase behavior of sodium alkyl benzene sulfonate/water mixtures. | 2007 Jan 16 |
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Silica-supported sodium sulfonate with ionic liquid: a neutral catalyst system for Michael reactions of indoles in water. | 2007 Jan 18 |
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Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives. | 2007 Jan 8 |
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Histopathological changes in testis of the freshwater fish, Heteropneustes fossilis (Bloch) exposed to linear alkyl benzene sulphonate (LAS). | 2007 Jul |
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Testing organic solvents for the extraction from fish of sulfophenylcarboxylic acids, prior to determination by liquid chromatography-mass spectrometry. | 2007 Jul |
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Peripheral infusion of rat bone marrow derived endothelial progenitor cells leads to homing in acute lung injury. | 2007 Jul 9 |
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[Effects and mechanisms of inorganic anions in water on degradation of LAS by UV/H2 O2 combination process]. | 2007 Nov |
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R2(2)(8) motifs in Aminopyrimidine sulfonate/carboxylate interactions: crystal structures of pyrimethaminium benzenesulfonate monohydrate (2:2:1) and 2-amino-4,6-dimethylpyrimidinium sulfosalicylate dihydrate (4:2:2). | 2007 Nov 13 |
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Impact of surface derivatization of poly-L-lysine dendrimers with anionic arylsulfonate or succinate groups on intravenous pharmacokinetics and disposition. | 2007 Nov-Dec |
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In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase. | 2007 Oct |
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Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water. | 2007 Oct |
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Removal of anionic surfactants from aqueous solutions by adsorption onto high area activated carbon cloth studied by in situ UV spectroscopy. | 2007 Sep 5 |
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Polymeric zinc ferrocenyl sulfonate as a molecular aspirator for the removal of toxic metal ions. | 2008 |
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Simultaneous enantioseparation of antiparkinsonian medication Rotigotine and related chiral impurities by capillary zone electrophoresis using dual cyclodextrin system. | 2008 Apr 14 |
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Specifics of solvation of sulfonated polyelectrolytes in water, dimethylmethylphosphonate, and their mixture: a molecular simulation study. | 2008 Apr 28 |
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The reactor design and comparison of Fenton, electro-Fenton and photoelectro-Fenton processes for mineralization of benzene sulfonic acid (BSA). | 2008 Aug 15 |
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Evaluation of dicationic reagents for their use in detection of anions using positive ion mode ESI-MS via gas phase ion association. | 2008 Feb |
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J-aggregates of diprotonated tetrakis(4-sulfonatophenyl)porphyrin induced by ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate. | 2008 Jul 10 |
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Pseudomonas aeruginosa strain RW41 mineralizes 4-chlorobenzenesulfonate, the major polar by-product from DDT manufacturing. | 2008 Jun |
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On-target sample preparation of 4-sulfophenyl isothiocyanate-derivatized peptides using AnchorChip Targets. | 2008 Mar |
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Mixture toxicity of three toxicants with similar and dissimilar modes of action to Daphnia magna. | 2008 Mar |
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Evidence of PPII-like helical conformation and glass transition in a self-assembled solid-state polypeptide-surfactant complex: poly(L-histidine)/docylbenzenesulfonic acid. | 2008 May |
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Reduction of 2,3,5-triphenyl-2H-tetrazolium chloride in the presence of polyelectrolytes containing 4-styrenesulfonate moieties. | 2008 May 1 |
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Development and validation of RP-HPLC method for the determination of genotoxic alkyl benzenesulfonates in amlodipine besylate. | 2008 Sep 10 |
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Stacking of 2,3,5-triphenyl-2H-tetrazolium chloride onto polyelectrolytes containing 4-styrenesulfonate groups. | 2008 Sep 11 |
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Ultrasonic nebulization in aqueous solutions and the role of interfacial adsorption dynamics in surfactant enrichment. | 2008 Sep 16 |
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Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols. | 2008 Sep 5 |
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Interactions of lambda and delta enantiomers of ruthenium(II) cationic complexes with achiral anionic porphyrins. | 2009 Jan |
Patents
Sample Use Guides
Rat LD50 (oral) 890 mg/kg.
Wild bird LD50 (oral) 75 mg/kg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26529301
Biodegradation had been quantified in aqueous medium and P. fluorescens in agitated flasks experiments without sand matrix. The concentration of the MCs were determined every day (t=6 d for phenol, salicylic acid, and benzenesulfonic acid). Batch experiments were conducted in wide-neck bottles (Vinner = 250 ml) with defined moisture contents. The moisture content (θ) is the ratio between the volume of water and the total volume of the sample. To prevent unwanted strains from being included, the empty bottles were sterilized for t=20 min (T=121 °C) and the experimentswere done on a sterile bench. The sterilized bottles were filled with 40 g of sterilized sand (t = 20 min, T = 121 °C) each. The substrate solution was prepared by adding c0 (MC) = 0.5 mmol/l and nutrient solution to V = 1 l of deionized water. Each MC was investigated individually. In addition, the calculated volume of P. fluorescens solution was added. Five different moisture contents were used (θ = 5, 10, 24, 37 and 42%) by adding Vsubstrate = 1.3 to 12 ml (c0 (MC) = 0.5 mmol/l), inorganic medium and P. fluorescens (OD600=0.1, 7 × 107 cells/ml). The bottles were closed with a rubber stopper to prevent ambient air from entering and they were shaken slightly in the dark obtain a fairly homogeneous substrate distribution. The temperature was kept at T = 22 ±1 °C. The oxygen concentration was measured by sensor spots fixed to the inner glass surface of the bottles. After defined time periods (t=6 d or 60 d), 50 ml of deionized water (Millipore) were added with a dispenser and allwas shaken for t=1 min. The supernatantwas filtered (pore size 0.4 μm, polycarbonate) and prepared for analysis. Each bottle was “sacrificed” and each supernatant was analyzed once. For example, a triplicate experiment with five differentmoisture contents and a maximum reaction time of three days with daily control needed 45 bottles (3 × 5 × 3).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:15:42 GMT 2023
by
admin
on
Fri Dec 15 15:15:42 GMT 2023
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Record UNII |
685928Z18A
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
224900
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BENZENESULFONIC ACID
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