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)

pka

4.68±0.10(Predicted)

form 

Crystalline Powder and/or Chunks

color 

Yellow

Water Solubility 

Partly soluble in water and chloroform.

Sensitive 

Stench

BRN 

606924

CAS DataBase Reference

1849-36-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzenethiol, 4-nitro-(1849-36-1)

EPA Substance Registry System

4-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

F 

9-13-23

Hazard Note 

Harmful/Irritant/Stench

HazardClass 

IRRITANT

HS Code 

29309090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-Nitrothiophenol Usage And Synthesis

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.” 环境科学与技术 14 10 (1980): 1249–1253.

4-Nitrothiophenol(1849-36-1)Related Product Information

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