U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Effect of linear alkyl benzene sulphonate on erythrocyte sedimentation rate of teleost fish, Heteropneustes fossilis.
2002 Apr
Haematotoxic effect of linear alkyl benzene sulphonate (LAS) in fish, Heteropneustes fossilis.
2002 Jan
Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A.
2004 Apr 7
Preparation of natural alpha-tocopherol from non-alpha-tocopherols.
2004 Dec
Gene expression changes in peripheral blood-derived dendritic cells following exposure to a contact allergen.
2004 May 2
Silver(I) arylsulfonates: a systematic study of "softer" hybrid inorganic-organic solids.
2004 Oct 18
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of 4-sulfophenyl isothiocyanate-derivatized peptides on AnchorChip sample supports using the sodium-tolerant matrix 2,4,6-trihydroxyacetophenone and diammonium citrate.
2005
Fenton degradation of organic compounds promoted by dyes under visible irradiation.
2005 Aug 1
[Relation between oxygen uptake rate and biosorption of activated sludge against chemical substance].
2005 Feb
Determination of biodegradation products from sulfonated dyes by Pleurotus ostreatususing capillary electrophoresis coupled with mass spectrometry.
2005 Jan
Linear alkyl benzene sulphonate (LAS) degradation by immobilized Pseudomonas aeruginosa under low intensity ultrasound.
2005 Jan 15
Photo-cross-linked immobilization of polyelectrolytes for enzymatic construction of conductive nanocomposites.
2005 Jun 29
Discovery of CC chemokine receptor-3 (CCR3) antagonists with picomolar potency.
2005 Mar 24
Ab initio and DFT study of the geometric structures and static dipole (hyper)polarizabilities of aromatic anions.
2005 Nov 17
Ferromagnetic coupling promoted by kappa3N:kappa2N bridging system.
2006 Aug 7
Inhibition of (Na(+)/K(+))-ATPase by Cibacron Blue 3G-A and its analogues.
2006 Dec
Permeation flux of organic molecules through silica-surfactant nanochannels in a porous alumina membrane.
2006 Dec
Carbon-fiber microelectrodes modified with 4-sulfobenzene have increased sensitivity and selectivity for catecholamines.
2006 Feb 28
Enrichment of N-terminal sulfonated peptides by a water-soluble fullerene derivative and its applications to highly efficient proteomics.
2006 Jan 18
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
Acid-base equilibria in 5,10,15,20-tetrakis(4-sulfonatophenyl)chlorin: Role of conformational flexibility.
2006 Mar 16
Iron porphyrin-cyclodextrin supramolecular complex as a functional model of myoglobin in aqueous solution.
2006 May 29
Inorganic asymmetric synthesis: asymmetric synthesis of a two-bladed propeller, octahedral metal complex.
2006 Oct 16
A scalable machine-learning approach to recognize chemical names within large text databases.
2006 Sep 6
The behaviour of linear alkyl benzene sulphonate under direct discharge conditions in Vientiane, Lao PDR.
2007 Dec
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
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
Silica-supported sodium sulfonate with ionic liquid: a neutral catalyst system for Michael reactions of indoles in water.
2007 Jan 18
Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives.
2007 Jan 8
Histopathological changes in testis of the freshwater fish, Heteropneustes fossilis (Bloch) exposed to linear alkyl benzene sulphonate (LAS).
2007 Jul
Testing organic solvents for the extraction from fish of sulfophenylcarboxylic acids, prior to determination by liquid chromatography-mass spectrometry.
2007 Jul
[Effects and mechanisms of inorganic anions in water on degradation of LAS by UV/H2 O2 combination process].
2007 Nov
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
Impact of surface derivatization of poly-L-lysine dendrimers with anionic arylsulfonate or succinate groups on intravenous pharmacokinetics and disposition.
2007 Nov-Dec
In vitro effect of agriculture pollutants and their joint action on Pseudokirchneriella subcapitata acid phosphatase.
2007 Oct
Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water.
2007 Oct
Removal of anionic surfactants from aqueous solutions by adsorption onto high area activated carbon cloth studied by in situ UV spectroscopy.
2007 Sep 5
Polymeric zinc ferrocenyl sulfonate as a molecular aspirator for the removal of toxic metal ions.
2008
Simultaneous enantioseparation of antiparkinsonian medication Rotigotine and related chiral impurities by capillary zone electrophoresis using dual cyclodextrin system.
2008 Apr 14
Specifics of solvation of sulfonated polyelectrolytes in water, dimethylmethylphosphonate, and their mixture: a molecular simulation study.
2008 Apr 28
The reactor design and comparison of Fenton, electro-Fenton and photoelectro-Fenton processes for mineralization of benzene sulfonic acid (BSA).
2008 Aug 15
Evaluation of dicationic reagents for their use in detection of anions using positive ion mode ESI-MS via gas phase ion association.
2008 Feb
Pseudomonas aeruginosa strain RW41 mineralizes 4-chlorobenzenesulfonate, the major polar by-product from DDT manufacturing.
2008 Jun
On-target sample preparation of 4-sulfophenyl isothiocyanate-derivatized peptides using AnchorChip Targets.
2008 Mar
Mixture toxicity of three toxicants with similar and dissimilar modes of action to Daphnia magna.
2008 Mar
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
Development and validation of RP-HPLC method for the determination of genotoxic alkyl benzenesulfonates in amlodipine besylate.
2008 Sep 10
Stacking of 2,3,5-triphenyl-2H-tetrazolium chloride onto polyelectrolytes containing 4-styrenesulfonate groups.
2008 Sep 11
Ultrasonic nebulization in aqueous solutions and the role of interfacial adsorption dynamics in surfactant enrichment.
2008 Sep 16
Interactions of lambda and delta enantiomers of ruthenium(II) cationic complexes with achiral anionic porphyrins.
2009 Jan
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 Fri Dec 15 15:15:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:42 GMT 2023
Record UNII
685928Z18A
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZENESULFONIC ACID
HSDB   II   MI  
Systematic Name English
BENZENSULFONIC ACID
Systematic Name English
BENZENESULFONIC ACID [HSDB]
Common 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 Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
Code System Code Type Description
PUBCHEM
7371
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID9024568
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
RXCUI
993243
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
BENZENESULFONIC ACID
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
MESH
C032365
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
MERCK INDEX
m2341
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY Merck Index
HSDB
2642
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
EVMPD
SUB23114
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
SMS_ID
100000088622
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
NCI_THESAURUS
C80891
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
CAS
98-11-3
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
DAILYMED
685928Z18A
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
CONCEPT Industrial Aid
ECHA (EC/EINECS)
202-638-7
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
RXCUI
1313278
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
ALTERNATIVE
FDA UNII
685928Z18A
Created by admin on Fri Dec 15 15:15:42 GMT 2023 , Edited by admin on Fri Dec 15 15:15:42 GMT 2023
PRIMARY
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