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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
Structure of Benzenesulfonic acid

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)

HIDE SMILES / InChI

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

Description
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).

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Interactions of lambda and delta enantiomers of ruthenium(II) cationic complexes with achiral anionic porphyrins.
2009-01
Ultrasonic nebulization in aqueous solutions and the role of interfacial adsorption dynamics in surfactant enrichment.
2008-09-16
Stacking of 2,3,5-triphenyl-2H-tetrazolium chloride onto polyelectrolytes containing 4-styrenesulfonate groups.
2008-09-11
Development and validation of RP-HPLC method for the determination of genotoxic alkyl benzenesulfonates in amlodipine besylate.
2008-09-10
Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols.
2008-09-05
The reactor design and comparison of Fenton, electro-Fenton and photoelectro-Fenton processes for mineralization of benzene sulfonic acid (BSA).
2008-08-15
J-aggregates of diprotonated tetrakis(4-sulfonatophenyl)porphyrin induced by ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate.
2008-07-10
Pseudomonas aeruginosa strain RW41 mineralizes 4-chlorobenzenesulfonate, the major polar by-product from DDT manufacturing.
2008-06
Reduction of 2,3,5-triphenyl-2H-tetrazolium chloride in the presence of polyelectrolytes containing 4-styrenesulfonate moieties.
2008-05-01
Evidence of PPII-like helical conformation and glass transition in a self-assembled solid-state polypeptide-surfactant complex: poly(L-histidine)/docylbenzenesulfonic acid.
2008-05
Specifics of solvation of sulfonated polyelectrolytes in water, dimethylmethylphosphonate, and their mixture: a molecular simulation study.
2008-04-28
Simultaneous enantioseparation of antiparkinsonian medication Rotigotine and related chiral impurities by capillary zone electrophoresis using dual cyclodextrin system.
2008-04-14
On-target sample preparation of 4-sulfophenyl isothiocyanate-derivatized peptides using AnchorChip Targets.
2008-03
Mixture toxicity of three toxicants with similar and dissimilar modes of action to Daphnia magna.
2008-03
Evaluation of dicationic reagents for their use in detection of anions using positive ion mode ESI-MS via gas phase ion association.
2008-02
Polymeric zinc ferrocenyl sulfonate as a molecular aspirator for the removal of toxic metal ions.
2008
The behaviour of linear alkyl benzene sulphonate under direct discharge conditions in Vientiane, Lao PDR.
2007-12
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).
2007-11-13
[Effects and mechanisms of inorganic anions in water on degradation of LAS by UV/H2 O2 combination process].
2007-11
Impact of surface derivatization of poly-L-lysine dendrimers with anionic arylsulfonate or succinate groups on intravenous pharmacokinetics and disposition.
2007-10-24
In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase.
2007-10
Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water.
2007-10
Removal of anionic surfactants from aqueous solutions by adsorption onto high area activated carbon cloth studied by in situ UV spectroscopy.
2007-09-05
Study of biodegradation products from azo dyes in fungal degradation by capillary electrophoresis/electrospray mass spectrometry.
2007-08-03
Peripheral infusion of rat bone marrow derived endothelial progenitor cells leads to homing in acute lung injury.
2007-07-09
Histopathological changes in testis of the freshwater fish, Heteropneustes fossilis (Bloch) exposed to linear alkyl benzene sulphonate (LAS).
2007-07
Testing organic solvents for the extraction from fish of sulfophenylcarboxylic acids, prior to determination by liquid chromatography-mass spectrometry.
2007-07
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.
2007-02
Silica-supported sodium sulfonate with ionic liquid: a neutral catalyst system for Michael reactions of indoles in water.
2007-01-18
Lateral phase separation gives multiple lamellar phases in a "binary" surfactant/water system: the phase behavior of sodium alkyl benzene sulfonate/water mixtures.
2007-01-16
Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives.
2007-01-08
Inhibition of (Na(+)/K(+))-ATPase by Cibacron Blue 3G-A and its analogues.
2006-12
Permeation flux of organic molecules through silica-surfactant nanochannels in a porous alumina membrane.
2006-12
Hierarchical ionic self-assembly of rod-comb block copolypeptide-surfactant complexes.
2006-12
Inorganic asymmetric synthesis: asymmetric synthesis of a two-bladed propeller, octahedral metal complex.
2006-10-16
A scalable machine-learning approach to recognize chemical names within large text databases.
2006-09-06
Ferromagnetic coupling promoted by kappa3N:kappa2N bridging system.
2006-08-07
Low level determination of p-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry.
2006-06-30
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.
2006-06
Iron porphyrin-cyclodextrin supramolecular complex as a functional model of myoglobin in aqueous solution.
2006-05-29
Acid-base equilibria in 5,10,15,20-tetrakis(4-sulfonatophenyl)chlorin: Role of conformational flexibility.
2006-03-16
Carbon-fiber microelectrodes modified with 4-sulfobenzene have increased sensitivity and selectivity for catecholamines.
2006-02-28
Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid.
2006-02-03
Enrichment of N-terminal sulfonated peptides by a water-soluble fullerene derivative and its applications to highly efficient proteomics.
2006-01-18
Formation of drug-arylsulfonate complexes inside liposomes: a novel approach to improve drug retention.
2006-01-10
Dihydroxy-2,5 benzenesulphonate (dobesilate) elicits growth arrest and apoptosis in glioma cells.
2005-12
Ab initio and DFT study of the geometric structures and static dipole (hyper)polarizabilities of aromatic anions.
2005-11-17
Raman spectroscopic study of hydrogen bonding in benzenesulfonic acid/acrylonitrile solutions.
2005-10
Anaerobic digestion of linear alkyl benzene sulfonates: biodegradation kinetics and metabolite analysis.
2005-09
Fenton degradation of organic compounds promoted by dyes under visible irradiation.
2005-08-01
Patents

Patents

Sample Use Guides

Rat LD50 (oral) 890 mg/kg. Wild bird LD50 (oral) 75 mg/kg
Route of Administration: Oral
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 Mon Mar 31 17:51:59 GMT 2025
Edited
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on Mon Mar 31 17:51:59 GMT 2025
Record UNII
685928Z18A
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZENESULFONIC ACID [HSDB]
Preferred Name English
Benzenesulfonic acid
HSDB   II   MI  
Systematic Name English
BENZENSULFONIC ACID
Systematic Name English
BENZENESULFONATE
Common Name English
BENZENESULFONIC ACID [II]
Common Name English
BENZENESULFONIC ACID [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 224900
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
Code System Code Type Description
PUBCHEM
7371
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID9024568
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
RXCUI
993243
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
BENZENESULFONIC ACID
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
MESH
C032365
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
MERCK INDEX
m2341
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY Merck Index
HSDB
2642
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
EVMPD
SUB23114
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
SMS_ID
100000088622
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
NCI_THESAURUS
C80891
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
CAS
98-11-3
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
DAILYMED
685928Z18A
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
CONCEPT Industrial Aid
ECHA (EC/EINECS)
202-638-7
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
RXCUI
1313278
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
ALTERNATIVE
FDA UNII
685928Z18A
Created by admin on Mon Mar 31 17:51:59 GMT 2025 , Edited by admin on Mon Mar 31 17:51:59 GMT 2025
PRIMARY
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