Structure via PubChem · Public domain (PubChem)
thiophenol
Sign in to saveAlso known as benzenethiol, mercaptobenzene, phenyl mercaptan, phenylthiol
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.
Chemical data
- Formula
- C6H6S
- Molecular weight
- 110.18 g/mol
- IUPAC name
- benzenethiol
- SMILES
- C1=CC=C(C=C1)S
- InChIKey
- RMVRSNDYEFQCLF-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,312 papers- Recent Progress in the Development of Fluorescent Probes for Thiophenol.Molecules (Basel, Switzerland) · 2019
- Thiophenol detection using an AIE fluorescent probe through self-assembly with TPE-based glycoclusters.Organic & biomolecular chemistry · 2019
- Monitoring the Thiol/Thiophenol Molecule-Modulated Plasmon-Mediated Silver Oxidation with Dark-Field Optical Microscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
- Are thiophenol based small molecular weight nickel complexes sufficient mimics of the NiSOD enzyme?Dalton transactions (Cambridge, England : 2003) · 2025
- Thiophenol-Modified Fluorographene Derivatives for Nonlinear Optical Applications.ChemPlusChem · 2019
via PubMed
Wikidata facts
- Mass
- 110.019
Show 17 more facts
- boiling point
- 169.1
- density
- 1.08
- NIOSH Pocket Guide ID
- 0050
- melting point
- -14.9
- vapor pressure
- 1
- flash point
- 132
- solubility
- 0.08
- ionization energy
- 8.30
- ceiling exposure limit
- 0.5
- median lethal dose (LD50)
- 300
- minimal lethal dose
- 302
- time-weighted average exposure limit
- 2
- short-term exposure limit
- 0.2
- chemical formula
- C₆H₆S
- canonical SMILES
- C1=CC=C(C=C1)S
- Commons category
- Thiophenol
- median lethal concentration (LC50)
- 33
via Wikidata · CC0
~4 min read
Article
11 sectionsContents
- Synthesis
- Applications
- Properties and reactions
- Acidity
- Alkylation
- Oxidation
- Chlorination
- Coordination to metals
- Safety
- References
- External links
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.