4-Nitrothiophenol Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Nitrothiophenol Chemical Properties,Usage,Production

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.