Benzenesulfonic acid

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Benzenesulfonic acid

  • Name Benzenesulfonic acid
  • CAS 98-11-3
  • Purity 99%
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Product Details

Cost-effective and customizable Benzenesulfonic acid 98-11-3 supplier

  • Molecular Formula: C6H6O3S
  • Molecular Weight: 158.178
  • Appearance/Colour: green solid 
  • Vapor Pressure: 3.07E-08mmHg at 25°C 
  • Melting Point: 30-60 °C 
  • Refractive Index: 1.5151 (estimate) 
  • Boiling Point: 137℃ 
  • PKA: 0.7(at 25℃) 
  • Flash Point: >230°F 
  • PSA: 62.75000 
  • Density: 1.409 g/cm3 
  • LogP: 2.01410 

Benzenesulfonic acid(Cas 98-11-3) Usage

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.".

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

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.]

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.

Definition

ChEBI: The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.

General Description

Deliquescent needles or large plates.

InChI:InChI=1/C6H6O3S.H2O/c7-10(8,9)6-4-2-1-3-5-6;/h1-5H,(H,7,8,9);1H2

98-11-3 Relevant articles

-

Lisk

, p. 1671,1674, 1678 (1948)

-

-

Hochstetter

, p. 549 (1898)

-

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, p. 25811 - 25815 (2021/08/09)

Electrochemical reduction of different a...

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Aryl and alkyl sulfonic acid compounds as well as construction method adopting inorganic sulfur salt and application

-

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The invention discloses aryl and alkyl s...

98-11-3 Process route

<i>N</i>-methyl-<i>N</i>-nitro-benzenesulfonamide
59263-03-5

N -methyl-N -nitro-benzenesulfonamide

methanol
67-56-1

methanol

methyl(phenylsulfonyl)amide
5183-78-8

methyl(phenylsulfonyl)amide

benzenesulfonic acid
98-11-3

benzenesulfonic acid

Conditions
Conditions Yield
With sulfuric acid; In water; at 25 ℃; Rate constant; Dependence of the decomposition rate on concentration of H2SO4;
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

3-Aminophenyl-benzolsulfonat
26408-93-5

3-Aminophenyl-benzolsulfonat

1-Benzolsulfamino-3-benzolsulfoxy-benzol
75383-59-4

1-Benzolsulfamino-3-benzolsulfoxy-benzol

N-(3-hydroxyphenyl)-p-toluenesulfonylamide
59149-19-8

N-(3-hydroxyphenyl)-p-toluenesulfonylamide

benzenesulfonic acid
98-11-3

benzenesulfonic acid

Conditions
Conditions Yield
With sodium hydroxide; sodium carbonate; In water; at 35 - 40 ℃; Product distribution; other solvents, other catalysts;
30%
20%
30%

98-11-3 Upstream products

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    67-56-1

    methanol

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    4-diazobenzenesulfonic acid

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    m-sulfanilic acid diazonium salt

  • 56-23-5
    56-23-5

    tetrachloromethane

98-11-3 Downstream products

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    98-55-5

    terpineol

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    29754-47-0

    pyridinium para-toluene sulfonate

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    2643-30-3

    3-Vinylquinuclidine

  • 6667-90-9
    6667-90-9

    (E)-3-ethylidenequinuclidine

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