Thiophenol in Organic Synthesis: Facilitating Thioether and Disulfide Formation
Thiophenol, identified by CAS number 108-98-5 and commonly known as Benzenethiol or Phenyl Mercaptan, is a cornerstone reagent in organic synthesis, particularly for its role in creating thioether and disulfide linkages. NINGBO INNO PHARMCHEM CO.,LTD. provides high-purity Thiophenol, enabling chemists to achieve precise synthetic outcomes.
The utility of Thiophenol in forming thioethers is a key aspect of its application. When treated with a base, Thiophenol readily forms the thiophenolate anion (PhS⁻), a highly nucleophilic species. This anion can then undergo facile alkylation with alkyl halides or other electrophiles to produce phenyl alkyl sulfides, commonly known as thioethers. For instance, the reaction of sodium thiophenolate with methyl iodide yields methyl phenyl sulfide, also called thioanisole. This process is generally irreversible and highly efficient, making Thiophenol a preferred starting material for synthesizing a wide range of thioether compounds. These thioethers are valuable intermediates in the synthesis of pharmaceuticals, agrochemicals, and materials science.
Thiophenol is also integral to the formation of disulfides, specifically diphenyl disulfide (PhS-SPh). In the presence of an oxidizing agent, or even atmospheric oxygen under basic conditions, two molecules of Thiophenol can couple to form the disulfide bond. This oxidation reaction is often easily reversible, with the disulfide being reducible back to the thiol using mild reducing agents like sodium borohydride. This redox cycling capability of Thiophenol is exploited in various synthetic strategies and as a source of hydrogen atoms in certain reactions.
The acidity of Thiophenol (pKa ~6.6) is notably higher than that of phenol (pKa ~9.9), which contributes to the ease of thiophenolate formation and its subsequent reactivity. This enhanced acidity, along with the nucleophilicity of the thiolate anion, makes Thiophenol a more reactive and versatile reagent in many synthetic pathways compared to its oxygen analog.
NINGBO INNO PHARMCHEM CO.,LTD. supplies Thiophenol that is ideal for these demanding synthetic applications. Our commitment to quality assurance ensures that chemists and manufacturers can rely on the consistency and purity of our products for their critical organic synthesis needs. Whether for complex pharmaceutical intermediates or specialty chemicals, Thiophenol from NINGBO INNO PHARMCHEM CO.,LTD. is a reliable choice.
The utility of Thiophenol in forming thioethers is a key aspect of its application. When treated with a base, Thiophenol readily forms the thiophenolate anion (PhS⁻), a highly nucleophilic species. This anion can then undergo facile alkylation with alkyl halides or other electrophiles to produce phenyl alkyl sulfides, commonly known as thioethers. For instance, the reaction of sodium thiophenolate with methyl iodide yields methyl phenyl sulfide, also called thioanisole. This process is generally irreversible and highly efficient, making Thiophenol a preferred starting material for synthesizing a wide range of thioether compounds. These thioethers are valuable intermediates in the synthesis of pharmaceuticals, agrochemicals, and materials science.
Thiophenol is also integral to the formation of disulfides, specifically diphenyl disulfide (PhS-SPh). In the presence of an oxidizing agent, or even atmospheric oxygen under basic conditions, two molecules of Thiophenol can couple to form the disulfide bond. This oxidation reaction is often easily reversible, with the disulfide being reducible back to the thiol using mild reducing agents like sodium borohydride. This redox cycling capability of Thiophenol is exploited in various synthetic strategies and as a source of hydrogen atoms in certain reactions.
The acidity of Thiophenol (pKa ~6.6) is notably higher than that of phenol (pKa ~9.9), which contributes to the ease of thiophenolate formation and its subsequent reactivity. This enhanced acidity, along with the nucleophilicity of the thiolate anion, makes Thiophenol a more reactive and versatile reagent in many synthetic pathways compared to its oxygen analog.
NINGBO INNO PHARMCHEM CO.,LTD. supplies Thiophenol that is ideal for these demanding synthetic applications. Our commitment to quality assurance ensures that chemists and manufacturers can rely on the consistency and purity of our products for their critical organic synthesis needs. Whether for complex pharmaceutical intermediates or specialty chemicals, Thiophenol from NINGBO INNO PHARMCHEM CO.,LTD. is a reliable choice.
Perspectives & Insights
Chem Catalyst Pro
“9), which contributes to the ease of thiophenolate formation and its subsequent reactivity.”
Agile Thinker 7
“This enhanced acidity, along with the nucleophilicity of the thiolate anion, makes Thiophenol a more reactive and versatile reagent in many synthetic pathways compared to its oxygen analog.”
Logic Spark 24
“Our commitment to quality assurance ensures that chemists and manufacturers can rely on the consistency and purity of our products for their critical organic synthesis needs.”