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Indole-3-thiol

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Identification
Molecular formula
C8H7NS
CAS number
30732-59-9
IUPAC name
1H-indole-3-thiol
State
State

Indole-3-thiol typically exists as a crystalline solid at room temperature.

Melting point (Celsius)
50.00
Melting point (Kelvin)
323.15
Boiling point (Celsius)
272.00
Boiling point (Kelvin)
545.15
General information
Molecular weight
149.20g/mol
Molar mass
149.2040g/mol
Density
1.2600g/cm3
Appearence

Indole-3-thiol is a colorless to pale yellow crystalline solid. It is known for its distinctive aromatic odor.

Comment on solubility

Solubility of 1H-indole-3-thiol

1H-indole-3-thiol, a compound with the molecular formula C8H7NS, presents some intriguing solubility characteristics that are worth discussing.

Water Solubility

This compound exhibits limited solubility in water, influenced by its structure which includes an aromatic indole group and a thiol group. Typically, thiol compounds are less polar, resulting in reduced interactions with water molecules.

Organic Solvents

1H-indole-3-thiol is much more soluble in organic solvents. It can easily dissolve in:

  • Alcohols (e.g., ethanol, methanol)
  • Dimethyl sulfoxide (DMSO)
  • Apolar solvents (e.g., dichloromethane, hexane)

The solubility in these solvents is attributed to hydrophobic interactions and the ability of the thiol group to engage in hydrogen bonding.

Influence of pH

The solubility of 1H-indole-3-thiol can also be influenced by the pH of the solution:

  • In acidic conditions, it tends to be protonated, enhancing its solubility.
  • In neutral to basic conditions, the solubility may decrease due to reduced protonation.

Overall, understanding the solubility profile of 1H-indole-3-thiol is crucial for applications in organic synthesis and the pharmaceutical field. As the saying goes, "Like dissolves like," and in the case of this thiol compound, it finds its home within organic rather than aqueous environments.

Interesting facts

Interesting Facts about 1H-Indole-3-thiol

1H-indole-3-thiol, an intriguing compound in the realm of organic chemistry, is best known for its unique structural and functional properties. Here are some captivating insights about this chemical:

  • Biological Significance: This compound is widely studied for its role in biological systems. It has been linked to various biological activities such as antimicrobial and anticancer properties. The presence of the thiol group contributes to its reactivity and potential medicinal applications.
  • Pharmaceutical Potential: Research has shown that 1H-indole-3-thiol derivatives exhibit potential in drug development. They are being explored for their effectiveness against certain diseases, including cancer and neurological disorders.
  • Stability and Reactivity: The presence of the indole ring offers a stable yet reactive scaffold, making it a versatile building block in organic synthesis. The thiol group enhances its nucleophilicity, which is beneficial in various chemical reactions.
  • Natural Occurrence: Compounds related to indole-3-thiol are found in nature, particularly in plants. They are part of the complex chemical arsenal that plants use for defense against pests and pathogens.
  • Research Frontiers: Ongoing studies are delving into the environmental impact of 1H-indole-3-thiol and its derivatives, particularly in relation to their ecological role in plant biology.

This compound exemplifies how a seemingly simple structure can hold >great potential for scientific breakthroughs and applications in medicine and agriculture. As research progresses, its multifaceted properties continue to inspire scientists across various fields.

Synonyms
1H-INDOLE-3-THIOL
3-Mercaptoindole
480-94-4
BRN 0114958
DTXSID90197392
5-21-03-00010 (Beilstein Handbook Reference)
DTXCID00119883
1H-Indol-3-ylhydrosulfide
3-Thio-1H-indole
3-Indoylthiol
3-Sulfanylindole
3-mercapto-indole
MFCD00152110
1H-Indol-3-yl hydrosulfide
3-mercaptoindole, AldrichCPR
SCHEMBL154499
LYFRUBQVZGVXPR-UHFFFAOYSA-N
AKOS005070030
CS-0313514
H10966
1X-5008