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Indirubin-5-bromo-3-hydroxyindole

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Identification
Molecular formula
C16H9BrN2O2
CAS number
574758-30-8
IUPAC name
2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one
State
State

At room temperature, the compound is usually found as a crystalline solid.

Melting point (Celsius)
320.00
Melting point (Kelvin)
593.15
Boiling point (Celsius)
655.00
Boiling point (Kelvin)
928.15
General information
Molecular weight
348.16g/mol
Molar mass
348.0930g/mol
Density
1.7500g/cm3
Appearence

The compound commonly shows as a crystalline solid. It may appear in various shades of color depending on purity and form, often presenting as off-white to light-orange color. The precise appearance can be influenced by manufacturing impurities and physical state modifications.

Comment on solubility

Solubility of 2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one

The solubility of 2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one can be quite intriguing, primarily due to its complex aromatic structure. Generally, solubility can be significantly influenced by several factors:

  • Polarity: Compounds with polar functional groups tend to be more soluble in polar solvents. In this compound, the presence of the hydroxyl (-OH) group enhances its interaction with water, potentially increasing solubility.
  • Hydrogen Bonding: The hydroxyl group can engage in hydrogen bonding, which may facilitate dissolution in water. This property often suggests better solubility in aqueous solutions when compared to non-polar solvents.
  • Hydrophobic Interactions: The indole moieties may exhibit hydrophobic characteristics, which can impact solubility in organic solvents. Thus, while the compound may dissolve well in certain organic solvents, it could display limited solubility in water.
  • Temperature: As with many organic compounds, solubility can vary with temperature. Increased temperatures typically enhance solubility, so it is worth noting that heating the solution might improve the solubility of this compound.

In conclusion, while 2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one may show some potential for solubility in polar solvents due to its hydroxyl group, the presence of hydrophobic regions could lead to variability in solubility depending on the solvent and environmental conditions. As always, empirical testing should be conducted to determine actual solubility values.

Interesting facts

Interesting Facts about 2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one

This compound, known as a derivative of indole, is part of a fascinating class of organic molecules that often exhibit unique biological activities. Here are some intriguing highlights:

  • Indole Backbone: The indole structure is highly significant in medicinal chemistry, often serving as a core framework in a variety of pharmaceuticals. Its aromatic system contributes to the compound's ability to engage in effective biochemical interactions.
  • Biological Relevance: Compounds related to indole derivatives are known to possess various pharmacological properties. Research has indicated potential anticancer and antimicrobial activities, making this compound a subject of interest in drug development.
  • Substituent Influence: The presence of the 5-bromo and 3-hydroxy groups plays a critical role in modulating the compound's chemical reactivity and biological activity. Bromine, for instance, is known to enhance lipid solubility, which can improve the compound's bioavailability.
  • Research Applications: Scientists have been investigating compounds like this one for their roles in signaling pathways, especially those involving *serotonin* and *neurotransmitter* modulation, which are important for neurological function.
  • Synthesis Challenges: The synthetic routes to construct such complex molecules can involve multiple steps, often needing advanced techniques like *C-H activation* or *cross-coupling reactions*, showcasing the ingenuity required in modern organic synthesis.

In summary, 2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one embodies the intricacies and potential of indole chemistry, representing both a challenge and an opportunity for researchers in the field.

Synonyms
Bromindigo R
6492-73-5
3H-Indol-3-one, 5-bromo-2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-
2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one
5-Bromindigo
FJLJDIMWPQJEQK-YPKPFQOOSA-N
HICSZRHAFWZDGQ-UHFFFAOYSA-N
DTXSID201031723
3H-indol-3-one,5-bromo-2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-