98-11-3 Usage
Description
Benzene sulfonic acid is an organo sulfur compound with the formula C6H5SO3H. It is the simplest aromatic sulfonic acid. It forms colorless deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in carbon disulfide and diethyl ether. It is often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic.
Uses
Different sources of media describe the Uses of 98-11-3 differently. You can refer to the following data:
1. Benzenesulfonic acid is mainly consumed by conversion to other specialty chemicals. A variety of pharmaceutical drugs are prepared as salts of benzenesulfonic acid and are known as besylates or besilates. The alkali metal salt of benzenesulfonic acid was once widely used in the production of phenol. It acts as an acid catalyst for direct esterification of amino acids and peptides.
2. Benzenesulfonic acid is an aryl sulfonic acid that can be used to form an organic salt with 5,7-dimethyl-1,8-naphthyridine-2-amine, that can be a synthon for developing supramolecular structures. It can also act as a dopant for the polymerization of pyrrole to form poly(pyrrole), a conducting polymer useful in the development of flexible capacitors.
Application
The alkali metal salt of benzene sulfonic acid was once widely used in the production of phenol : C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3 C6H5ONa + HCl → C6H5OH + NaCl The process has been largely displaced by the Hock process, which generates less waste. Benzene sulfonic acid is mainly consumed by conversion to other specialty chemicals. A variety of pharmaceutical drugs are prepared as salts of benzene sulfonic acid and are known as besylates or besilates.
Preparation
Benzene sulfonic acid is prepared from the sulfonation of benzene using concentrated sulfuric acid : This conversion illustrates aromatic sulfonation, which has been called "one of the most important reactions in industrial organic chemistry.".
Definition
Different sources of media describe the Definition of 98-11-3 differently. You can refer to the following data:
1. ChEBI: The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.
2. A white crystalline
acid made by sulfonation of benzene. Any
further substitution onto the benzene ring
is directed into the 3 position.
3. benzenesulphonic acid: A colourlessdeliquescent solid, C6H5SO2OH,m.p. 43–44°C, usually found as anoily liquid. It is made by treating benzenewith concentrated sulphuricacid. Its alkyl derivatives are used asdetergents.
Reactions
Benzene sulfonic acid exhibits the reactions typical of other aromatic sulfonic acids, forming sulfonamides , sulfonyl chloride, and esters. The sulfonation is reversed above 220 °C. Dehydration with phosphorus pentoxide gives benzene sulfonic acid anhydride ((C6H5SO2)2O). Conversion to the corresponding benzene sulfonyl chloride (C6H5SO2Cl) is effected with phosphorus penta chloride. It is a strong acid, being dissociated in water.
Synthesis Reference(s)
The Journal of Organic Chemistry, 61, p. 1530, 1996 DOI: 10.1021/jo9520710Tetrahedron Letters, 19, p. 1211, 1978 DOI: 10.1016/S0040-4039(01)94501-0
General Description
Deliquescent needles or large plates.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Benzenesulfonic acid reacts with bases and many organic compounds.
Fire Hazard
Flash point data for Benzenesulfonic acid are not available, however Benzenesulfonic acid is probably combustible.
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by ingestion,
sbn contact, and probably inhalation. A
severe skin and eye irritant. See also
SULFATES and SULFONATES.
Purification Methods
Purify benzenesulfonic acid by dissolving it in a small volume of distilled H2O and stirring with slightly less than the theoretical amount of BaCO3. When effervescence is complete and the solution is still acidic, filter off the insoluble barium benzenesulfonate. The salt is collected and dried to constant weight in vacuo, then suspended in H2O and stirred with a little less than the equivalent (half mol.) of sulfuric acid. The insoluble BaSO4 (containing a little barium benzenesulfonate) is filtered off and the filtrate containing the free acid is evaporated in a high vacuum. The oily residue will eventually crystallise when completely anhydrous. A 32% commercial acid is allowed to fractionally crystallise at room temperature over P2O5 in a vacuum desiccator giving finally colourless deliquescent plates m 52.5o. The anhydrous crystalline acid is deliquescent and should be stored over anhydrous Na2SO4 in the dark and should be used in subdued sunlight as it darkens under sunlight. The main impurity is Fe which readily separates as the Fe salt in the early fractions [Taylor & Vincent J Chem Soc 3218 1952]. The S-benzylisothiuronium salt has m 148o (from EtOH/H2O). It is an IRRITANT to the skin and eyes. [See Adams & Marvel Org Synth Coll Vol I 84 1941, Michael & Adair Chem Ber 10 585 1877, Beilstein 11 IV 27.]
Check Digit Verification of cas no
The CAS Registry Mumber 98-11-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 98-11:
(4*9)+(3*8)+(2*1)+(1*1)=63
63 % 10 = 3
So 98-11-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O3S.H2O/c7-10(8,9)6-4-2-1-3-5-6;/h1-5H,(H,7,8,9);1H2
98-11-3Relevant articles and documents
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Lisk
, p. 1671,1674, 1678 (1948)
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Spontaneous Oxidation of Aromatic Sulfones to Sulfonic Acids in Microdroplets
Cooks, R. Graham,Psimos, Michael D.,Qiu, Lingqi
, (2022/04/07)
Reactions in microdroplets can be accelerated and can present unique chemistry compared to reactions in bulk solution. Here, we report the accelerated oxidation of aromatic sulfones to sulfonic acids in microdroplets under ambient conditions without the addition of acid, base, or catalyst. The experimental data suggest that the water radical cation, (H2O)+?, derived from traces of water in the solvent, is the oxidant. The substrate scope of the reaction indicates the need for a strong electron-donating group (e.g., p-hydroxyl) in the aromatic ring. An analogous oxidation is observed in an aromatic ketone with benzoic acid production. The shared mechanism is suggested to involve field-assisted ionization of water at the droplet/air interface, its reaction with the sulfone (M) to form the radical cation adduct, (M + H2O)+?, followed by 1,2-aryl migration and C-O cleavage. A remarkably high reaction rate acceleration (～103) and regioselectivity (～100-fold) characterize the reaction.
Aryl and alkyl sulfonic acid compounds as well as construction method adopting inorganic sulfur salt and application
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Paragraph 0046-0049; 0055-0058, (2020/09/16)
The invention discloses aryl and alkyl sulfonic acid compounds as shown in a formula (1) and a synthesis method thereof. The method comprises the following step: aromatic iodine and an inorganic sulfur source or alkyl bromide and an inorganic sulfur source as reaction raw materials react in a solvent under the action of alkali, a catalyst or an additive to obtain a series of aryl and alkyl sulfonic acid compounds. According to the method, the aryl and alkyl sulfonic acid compounds are constructed in one step by taking an inorganic sulfur reagent as a sulfur source, so that the defect of the mode in which the aryl and alkyl sulfonic acid compounds are synthesized by taking concentrated sulfuric acid, chlorosulfonic acid or sulfur dioxide gas and the like as sulfonating reagents in the priorart is avoided. The aryl and alkyl sulfonic acid compounds developed by the invention can be used for synthesizing aryl and alkyl sulfonic acid drug analogues.
Discovery of a Gut-Restricted JAK Inhibitor for the Treatment of Inflammatory Bowel Disease
Leonard, Kristi A.,Madge, Lisa A.,Krawczuk, Paul J.,Wang, Aihua,Kreutter, Kevin D.,Bacani, Genesis M.,Chai, Wenying,Smith, Russell C.,Tichenor, Mark S.,Harris, Michael C.,Malaviya, Ravi,Seierstad, Mark,Johnson, Marguerite E.,Venable, Jennifer D.,Kim, Suzie,Hirst, Gavin C.,Mathur, Ashok S.,Rao, Tadimeti S.,Edwards, James P.,Rizzolio, Michele C.,Koudriakova, Tatiana
, p. 2915 - 2929 (2020/04/08)
To identify Janus kinase (JAK) inhibitors that selectively target gastrointestinal tissues with limited systemic exposures, a class of imidazopyrrolopyridines with a range of physical properties was prepared and evaluated. We identified compounds with low intrinsic permeability and determined a correlation between permeability and physicochemical properties, clogP and tPSA, for a subset of compounds. This low intrinsic permeability translated into compounds displaying high colonic exposure and low systemic exposure after oral dosing at 25 mg/kg in mouse. In a mouse PK/PD model, oral dosing of lead compound 2 demonstrated dose-dependent inhibition of pSTAT phosphorylation in colonic explants post-oral dose but low systemic exposure and no measurable systemic pharmacodynamic activity. We thus demonstrate the utility of JAK inhibitors with low intrinsic permeability as a feasible approach to develop gut-restricted, pharmacologically active molecules with a potential advantage over systemically available compounds that are limited by systemic on-target adverse events.
