Chemical Properties
yellow crystalline powder and/or chunks
Uses
4-Nitrothiophenol has been used in the synthesis of dual emission fluorescent probe for the differential sensing of of glutathione (GSH) and cysteine/homocysteine (Cys/Hcy).
pNTP can also be used to synthesize diaryl thioethers via copper-catalyzed C-S coupling reaction.
Research
A 4-nitrothiophenol (4-NTP, Ar-NO2) modified electrode was prepared by dipping a gold electrode into a 4-NTP/dichloromethane solution (self-assembly method). The redox response of the electrode depended on the reduction stages of the nitro group in the 4-NTP molecule. When the 4-NTP on the electrode was partially reduced to 4-hydroxylaminothiophenol (Ar-NHOH) at -0.2 to -0.3 V vs SCE (the potential depends on the pH of the electrolyte solution), the electrode showed a pair of redox responses in an acidic aqueous solution. The responses are attributed to the redox cycling between 4-nitrosothiophenol (Ar-NO) and Ar-NHOH with two-electron and two-proton transfer.
Underpotential deposition (UPD) in electrochemistry can be used to form heterometal deposits on substrates at a monolayer level, altering the surface characteristics. For a monolayer of 4-nitrothiophenol (4-NTP) on a roughened Au substrate, the reduction and dimerization to 4,4′-dimercaptoazobenzene (DMAB) were monitored under conditions of Ag UPD using electrochemical surface-enhanced Raman spectroscopy (EC-SERS). Formation of DMAB was enhanced on the Ag surface deposited via UPD between the Au substrate and the 4-NTP layer. The structures of the 4-NTP layer and the plasmonic surface remained intact during Ag UPD[1-2].
References
[1] Misun Hong. "Underpotential Deposition of Silver on Gold for Surface Catalysis of Plasmon-Enhanced Reduction of 4-Nitrothiophenol." The Journal of Physical Chemistry C 125 30 (2021): 16569–16575.
[2] Hiromori Tsutsumi. "Electrochemical Behavior of a 4-Nitrothiophenol Modified Electrode Prepared by the Self-Assembly Method." Journal of Colloid and Interface Science 171 2 (1995): Pages 505-511.
[3] Jan Kozisek . "Plasmon-driven substitution of 4–mercaptophenylboronic acid to 4-nitrothiophenol monitored by surface-enhanced Raman spectroscopy." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 319 (2024): Article 124523.
[4] Satish C. Agarwal. “Reaction of epoxides with 4-nitrothiophenol. Its possible application for trapping and characterization of epoxides.” Environmental Science and Technology 14 10 (1980): 1249–1253.
