Skip to main content

3-Mercaptopyridine

ADVERTISEMENT
Identification
Molecular formula
C5H5NS
CAS number
1121-31-9
IUPAC name
pyridine-3-thiol
State
State

At room temperature, 3-mercaptopyridine is typically a solid. It crystallizes in a range from light yellow to brown and is stable under normal conditions. However, due to its thiol content, it should be handled with care to avoid exposure to its pungent odor.

Melting point (Celsius)
105.00
Melting point (Kelvin)
378.15
Boiling point (Celsius)
216.00
Boiling point (Kelvin)
489.15
General information
Molecular weight
111.16g/mol
Molar mass
111.1540g/mol
Density
1.1910g/cm3
Appearence

3-Mercaptopyridine typically appears as a light yellow to brown crystalline solid. It is known to have a distinctive and strong odor, reminiscent of sulfur compounds, due to the presence of the thiol group.

Comment on solubility

Solubility of Pyridine-3-thiol

Pyridine-3-thiol, with the chemical formula C5H5NS, exhibits notable solubility characteristics that are of interest to chemists. Understanding the solubility of this compound can be beneficial for various applications.

Solubility in Different Solvents:

Pyridine-3-thiol is relatively soluble in:

  • Polar solvents: It shows good solubility in water due to the presence of the thiol (-SH) group which can form hydrogen bonds.
  • Organic solvents: This compound is also soluble in organic solvents such as ethanol and methanol, enhancing its versatility in synthetic processes.

Factors Affecting Solubility:

Several factors influence the solubility of pyridine-3-thiol:

  • Temperature: Higher temperatures typically increase solubility in solids and liquids.
  • Presence of other ions: The solubility can be altered by the presence of salts or other compounds in solution.
  • pH levels: Changes in pH can affect the ionization of the thiol group, impacting solubility.

In conclusion, the solubility of pyridine-3-thiol is an essential consideration in its practical applications and research due to its unique structural properties. As with many compounds, understanding these solubility characteristics can pave the way for efficient and effective use in various chemical processes.

Interesting facts

Exploring Pyridine-3-Thiol

Pyridine-3-thiol, also known as 3-mercaptopyridine, is a fascinating compound that blends the properties of aromatic heterocycles with thiol functional groups, making it significant in various chemical and biological contexts.

Key Characteristics and Applications

  • Structural Features: Pyridine-3-thiol features a nitrogen atom incorporated within a six-membered aromatic ring. This unique structure contributes to its chemical reactivity and versatility in organic synthesis.
  • Chemical Reactivity: The thiol group (-SH) makes pyridine-3-thiol a strong nucleophile, allowing it to participate in a variety of chemical reactions, including S–N and S–C coupling reactions.
  • Biological Significance: Compounds containing thiol groups are known for their antioxidant properties. Pyridine-3-thiol can act as a protective agent against oxidative stress in biological systems.
  • Catalysis: In recent years, pyridine-3-thiol has been explored for its potential in catalyzing reactions, acting as a ligand in metal-catalyzed processes.

Fun Facts

  1. Natural Occurrence: Thiols, including pyridine-3-thiol, are often responsible for the characteristic odors of certain natural products, making them important in flavor and fragrance industries.
  2. Research Interests: Scientists are continually investigating pyridine-3-thiol for its role in coordination chemistry, particularly in its capacity to bind to transition metals, thereby influencing the development of new materials.
  3. Environmental Impact: The study of thiol compounds like pyridine-3-thiol is essential in understanding their potential roles as pollutants and their behaviors in different environments.

In conclusion, pyridine-3-thiol combines an intriguing structure with functional versatility, bridging gaps between synthetic chemistry, biological relevance, and environmental science.

Synonyms
3-PYRIDINETHIOL
3-Mercaptopyridine
16133-26-9
DTXSID30167115
DTXCID4089606
pyridine-3-thiol
MFCD00128263
5-Mercaptopyridine
BRN 0105737
Pyridine, 3-mercapto-
5-21-02-00091 (Beilstein Handbook Reference)
SCHEMBL263754
SCHEMBL263755
SCHEMBL959376
SCHEMBL4459697
SCHEMBL4465626
SCHEMBL4469649
SCHEMBL30022880
FFWJHVGUAKWTKW-UHFFFAOYSA-N
AT26584
SB21322
SY281596
CS-0265460
EN300-98716
InChI=1/C5H5NS/c7-5-2-1-3-6-4-5/h1-4,7