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4-Nitrothiophenol

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CAS:1849-36-1
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  • 4-NITROTHIOPHENOL
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  • CAS:1849-36-1
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  • 4-NITROBENZENETHIOL
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  • CAS:1849-36-1
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4-Nitrothiophenol Basic information
Product Name:4-Nitrothiophenol
Synonyms:Benzenethiol, p-nitro-;p-nitro-benzenethio;4-Nitrophenyl mercaptan;4-nitro-benzenethio;4-nitrothiophenolate;4-NITROBENZENETHIOL, TECH., 80%;p-Nitromercaptobenzene;4-NITROTHIOPHENOL
CAS:1849-36-1
MF:C6H5NO2S
MW:155.17
EINECS:217-436-4
Product Categories:Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles
Mol File:1849-36-1.mol
4-Nitrothiophenol Structure
4-Nitrothiophenol Chemical Properties
Melting point 72-77 °C (lit.)
Boiling point 281.9±23.0 °C(Predicted)
density 1.357 (estimate)
refractive index 1.5380 (estimate)
storage temp. 2-8°C
solubility Chloroform (Sparingly), Methanol (Slightly)
form Crystalline Powder and/or Chunks
pka4.68±0.10(Predicted)
color Yellow
Water Solubility Partly soluble in water and chloroform.
Sensitive Stench
BRN 606924
CAS DataBase Reference1849-36-1(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenethiol, 4-nitro-(1849-36-1)
EPA Substance Registry System4-Nitrothiophenol (1849-36-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR UN 3335
WGK Germany 3
RTECS DC1850000
9-13-23
Hazard Note Harmful/Irritant/Stench
HazardClass IRRITANT
HS Code 29309090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
4-Nitrothiophenol Usage And Synthesis
Chemical Propertiesyellow crystalline powder and/or chunks
Uses4-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.
ResearchA 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.” 环境科学与技术 14 10 (1980): 1249–1253.
Tag:4-Nitrothiophenol(1849-36-1) Related Product Information
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