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|Section2= |Section3= |Section8= }} Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colourless liquid is the simplest aromatic thiol. The chemical structures of thiophenols are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom. Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in the medicine thiomersal is a thiophenol. ==Synthesis== There are several methods of synthesis for thiophenol and related compounds, although thiophenol itself is usually purchased for laboratory operations. Methods are the reduction of benzenesulfonyl chloride with zinc.〔.〕 and the action of elemental sulfur on phenyl magnesium halide or phenyllithium followed by acidification. Via the Newman–Kwart rearrangement, phenols (1) can be converted to the thiophenols (5) by conversion to the O-aryl dialkylthiocarbamates (3), followed by heating to give the isomeric S-aryl derivative (4). 600px In the Leuckart thiophenol reaction the starting material is an aniline through the diazonium salt (ArN2X) and the xanthate (ArS(C=S)OR) 〔Leuckart, J. prakt. Chem., () 41, 189 (1890).〕〔D. S. Tarbell and D. K. Fukushima "m-Thiocresol" Org. Synth. 1947, volume 27, p. 81. 〕 Thiophenol can be manufactured from chlorobenzene and hydrogen sulfide over alumina at . The disulfide is the primary byproduct.〔 〕 The reaction medium is corrosive and requires ceramic or similar reactor lining. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「thiophenol」の詳細全文を読む スポンサード リンク
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