Thiophenol

Not to be confused with benzyl mercaptan.
Thiophenol
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Benzenethiol[1]
Other names
  • Thiophenol (or phenylthiol)
  • Phenyl mercaptan
  • Mercaptobenzene
Identifiers
3D model (JSmol)
506523
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.306 Edit this at Wikidata
EC Number
  • 203-635-3
RTECS number
  • DC0525000
UNII
  • InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H checkY
    Key: RMVRSNDYEFQCLF-UHFFFAOYSA-N checkY
  • InChI=1/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
    Key: RMVRSNDYEFQCLF-UHFFFAOYAL
  • Sc1ccccc1
Properties
C6H6S
Molar mass 110.17 g·mol−1
Appearance Colorless liquid
Odor Unpleasant, pungent
Density 1.0766 g/mL
Melting point −15 °C (5 °F; 258 K)
Boiling point 169 °C (336 °F; 442 K)
0.08%[2]
Solubility Most organic solvents; aqueous base
Vapor pressure 1 mmHg (18°C)[2]
Acidity (pKa)
-70.8·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H226, H300, H310, H314, H315, H330, H410
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
4
2
1
OX
Flash point 56 °C; 132 °F; 329 K[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 C 0.1 ppm (0.5 mg/m3) [15-minute][2]
IDLH (Immediate danger)
 N.D.[2]
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).
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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, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol 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.

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0050". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Cox, Brian G. Acids and Bases: Solvent Effects on Acid-base Strength. 1st ed. Oxford, UK: Oxford UP, 2013.
  4. ^ Bordwell, Frederick G.; Hughes, David L. (1982). "Thiol acidities and thiolate ion reactivities toward butyl chloride in dimethyl sulfoxide solution. The question of curvature in Broensted plots". The Journal of Organic Chemistry. 47 (17): 3224–3232. doi:10.1021/jo00138a005.