5-Bromo-6-chloro-1H-indol-3-yl octanoate
[CAS# 209347-94-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 5-Bromo-6-chloro-1H-indol-3-yl octanoate
• Synonyms: Octanoic acid 5-bromo-6-chloro-1H-indol-3-yl ester; Magenta C 8
• Molecular Formula: C₁₆H₁₉BrClNO₂
• Molecular Weight: 372.68
• CAS Registry Number: 209347-94-4
• SMILES: CCCCCCCC(=O)OC1=CNC2=CC(=C(C=C21)Br)Cl

Properties

• Solubility: Insoluble (5.6E^-4 g/L) (25 °C), Calc.^*
• Density: 1.397±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 482.6±40.0 °C 760 mmHg (Calc.)^*
• Flash point: 245.7±27.3 °C (Calc.)^*
• Index of refraction: 1.592 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

5-Bromo-6-chloro-1H-indol-3-yl octanoate is a chemically modified indole derivative characterized by bromine and chlorine substitutions at the 5 and 6 positions of the indole ring, respectively, and an octanoate ester group attached at the 3-position. The octanoate moiety is an eight-carbon fatty acid ester, which contributes to the molecule’s lipophilicity and alters its physical and chemical properties compared to the parent indole compound.

The synthesis of 5-bromo-6-chloro-1H-indol-3-yl octanoate typically involves halogenation reactions on the indole nucleus to introduce bromine and chlorine atoms selectively, followed by esterification at the 3-hydroxyl or 3-carboxyl site with octanoic acid or its derivatives. This synthetic pathway enables the production of a lipophilic ester suitable for applications where membrane permeability or interaction with hydrophobic environments is desired.

Applications of 5-bromo-6-chloro-1H-indol-3-yl octanoate are mainly found in biochemical and pharmaceutical research, where modified indole esters are employed as intermediates in the synthesis of more complex molecules or as potential bioactive agents. The lipophilic nature introduced by the octanoate ester may enhance cellular uptake or interaction with lipid membranes, which can be advantageous in drug design and delivery.

Compounds bearing halogen substitutions on the indole ring often exhibit biological activities such as antimicrobial, anticancer, or anti-inflammatory effects. The combination of halogenation and esterification in this molecule suggests potential use as a prodrug or as a molecular probe to study biological pathways involving indole derivatives.

In summary, 5-bromo-6-chloro-1H-indol-3-yl octanoate is a halogenated indole ester with enhanced lipophilicity due to its octanoate group. It serves primarily as a research tool or intermediate in chemical synthesis with potential implications in the development of biologically active compounds.

References

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