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Benzenesulfonic acid

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Benzenesulfonic acid
Structural formula of benzenesulfonic acid
Structural formula of benzenesulfonic acid
Ball-and-stick model
Ball-and-stick model
Names
Other names Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.399 Edit this at Wikidata
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)Key: SRSXLGNVWSONIS-UHFFFAOYSA-N
  • InChI=1/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)Key: SRSXLGNVWSONIS-UHFFFAOYAJ
SMILES
  • c1ccc(cc1)S(=O)(=O)O
Properties
Chemical formula C6H6O3S
Molar mass 158.17 g·mol
Appearance Colorless crystalline solid
Density 1.32 g/cm (47 °C)
Melting point * 44 °C (hydrate)
  • 51 °C (anhydrous)
Boiling point 190 °C (374 °F; 463 K)
Solubility in water Soluble
Solubility in other solvents Soluble in alcohol, insoluble in non-polar solvents
Acidity (pKa) -2.8
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Corrosive
Flash point >113 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Benzenesulfonic acid is an organic compound with the formula C6H5SO3H. It is the simplest aromatic sulfonic acid.

Benzenesulfonic acid 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. It has the ability to react violently with bases and attack metals.

Preparation

Benzenesulfonic acid is prepared from the aromatic sulfonation of benzene by concentrated sulfuric acid:

Aromatic sulfonation of benzene

Uses

The alkali metal salt of benzenesulfonic acid is used in the production of phenol and resorcinol. Benzenesulfonic acid is also used as an acidic catalyst in esterification and dehydration reactions.

Benzenesulfonic acid reacts with phosphorus pentoxide to form benzenesulfonic acid anhydride (C6H5SO2OSO2C6H5), and may be converted to the corresponding acid chloride benzenesulfonyl chloride (C6H5SO2Cl) with phosphorus pentachloride.

A variety of pharmaceutical drugs are prepared as salts of benzenesulfonic acid and are known as besylates or besilates.

References

  1. Benzenesulfonic acid, Sigma-Aldrich
  2. Guthrie, J. P. Hydrolysis of esters of oxy acids: pKa values for strong acids. Can. J. Chem. 1978, 56, 2342-2354.
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