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3-Nitrophenyl isothiocyanate

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Identification
Molecular formula
C7H4N2O2S
CAS number
2909-38-8
IUPAC name
1-isothiocyanato-3-nitro-benzene
State
State

At room temperature, 3-nitrophenyl isothiocyanate exists as a solid. With a somewhat low melting point, it can transition to a liquid form when mildly heated.

Melting point (Celsius)
57.00
Melting point (Kelvin)
330.15
Boiling point (Celsius)
289.00
Boiling point (Kelvin)
562.15
General information
Molecular weight
194.19g/mol
Molar mass
194.2040g/mol
Density
1.3620g/cm3
Appearence

3-Nitrophenyl isothiocyanate is a pale yellow solid with a crystalline appearance. The compound may display a slight luster and can appear as powder or small crystalline flakes.

Comment on solubility

Solubility of 1-isothiocyanato-3-nitro-benzene

1-isothiocyanato-3-nitro-benzene, also known by its IUPAC name, exhibits unique solubility characteristics that are influenced by its functional groups. The presence of both the isothiocyanate (-N=C=S) and nitro (-NO2) groups contributes to its overall solubility profile.

Factors Affecting Solubility

  • Polarity: The polar nature of the nitro group enhances its ability to interact with polar solvents, suggesting that it may show reasonable solubility in polar organic solvents.
  • Hydrogen Bonding: The isothiocyanate group can participate in hydrogen bonding, which may affect its solubility in solvents capable of such interactions.
  • Temperature: Solubility can also be temperature-dependent, often increasing with higher temperatures.

In general, 1-isothiocyanato-3-nitro-benzene is likely to be more soluble in:

  • Polar organic solvents (e.g., acetone, ethanol)
  • Dimethyl sulfoxide (DMSO) and similar solvents

However, it may have limited solubility in non-polar solvents due to the dual characteristics of its structure. Thus, when evaluating its solubility, it's crucial to consider solvent polarity and the temperature of the system.

Interesting facts

Interesting Facts About 1-Isothiocyanato-3-nitro-benzene

1-Isothiocyanato-3-nitro-benzene, often abbreviated as ITC-NB, is a fascinating compound that has garnered attention in various fields of research, particularly in medicinal chemistry and agricultural science. Here are some intriguing aspects of this compound:

  • Biological Activity: ITC-NB has been studied for its potential antimicrobial and antiparasitic properties, making it an interesting candidate in the search for new therapeutic agents.
  • Mechanism of Action: The presence of the isothiocyanate group is crucial, as it is known to interact with biological macromolecules, which can lead to a variety of cellular responses.
  • Role in Plant Defense: This compound is derived from natural sources like certain cruciferous vegetables and is believed to play a role in plant defense mechanisms against pests and diseases.
  • Synthesis: The synthesis of ITC-NB involves intriguing reactions, where nitroaniline derivatives are treated with thiophosgene or similar reagents to introduce the isothiocyanate functionality.
  • Potential Applications: Aside from its biological applications, research is ongoing into the potential use of ITC-NB in the development of novel agrochemicals to enhance crop protection.

In conclusion, 1-isothiocyanato-3-nitro-benzene stands out not just due to its chemical structure, but also because of its multifaceted roles in both natural and synthetic environments. As research continues to unfold, who knows what other exciting properties this compound might reveal?

Synonyms
3-Nitrophenyl isothiocyanate
3529-82-6
Benzene, 1-isothiocyanato-3-nitro-
BRN 2094061
DTXSID7063059
Phenyl, 3-nitro, isothiocyanate
3-12-00-01573 (Beilstein Handbook Reference)
DTXCID4038976
oezxlkszoawnju-uhfffaoysa-n
1-Isothiocyanato-3-nitrobenzene
m-Nitrophenyl isothiocyanate
MFCD00041245
ISOTHIOCYANIC ACID, m-NITROPHENYL ESTER
3-Nitrophenylisothiocyanate
1-isothiocyanato-3-nitro-benzene
m-Nitrophenylisothiocyanat
SCHEMBL1312153
1-Isothiocyanato-3-nitrobenzene #
3-Nitrophenyl isothiocyanate, 98%
DAA52982
AKOS015833376
LS-13250
SY012194
DB-048775
N1180
EN300-140686
F20945
A822717