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Benzenethiol

Thiophenol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Benzenethiol
Other names
Thiophenol
Phenyl mercaptan
Mercaptobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.306
PubChem CID
RTECS number DC0525000
UNII
Properties
C6H6S
Molar mass 110.17 g·mol−1
Appearance Colorless liquid
Odor Unpleasant, pungeant
Density 1.0766 g/mL
Melting point −15 °C (5 °F; 258 K)
Boiling point 169 °C (336 °F; 442 K)
0.08%
Solubility Most organic solvents; aqueous base
Vapor pressure 1 mmHg (18°C)
Acidity (pKa) 6.62 (H2O), 10 (DMSO)
-70.8·10−6 cm3/mol
Hazards
Main hazards Toxic
R-phrases (outdated) R10 R24/25 R26 R41
S-phrases (outdated) S23 S26 S28 S36/37/39 S45
Flash point 56 °C; 132 °F; 329 K
US health exposure limits (NIOSH):
PEL (Permissible)
none
REL (Recommended)
C 0.1 ppm (0.5 mg/m3) [15-minute]
IDLH (Immediate danger)
N.D.
Related compounds
Related thiols
1,2-Benzenedithiol
Benzenemethanethiol
Related compounds
Phenol
Benzeneselenol
Diphenyl disulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYNo ?)
Infobox references

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives 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.

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).

In the Leuckart thiophenol reaction, the starting material is an aniline through the diazonium salt (ArN2X) and the xanthate (ArS(C=S)OR). Alternatively, sodium sulfide and triazene can react in organic solutions and yield thiophenols.


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