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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
~4 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “thiophenol” article, available under the CC BY-SA 4.0 licence.