Overview
5-Bromoindolin-2-one is a brominated derivative of indolin-2-one, serving as a versatile building block in organic synthesis. Its molecular structure combines a bromine substituent at the 5-position with a lactam (cyclic amide) functional group, making it valuable for constructing complex heterocyclic compounds. Primarily used in pharmaceutical research, this intermediate enables modifications to the indole scaffold—a common motif in drug design. The bromine atom offers a reactive site for further cross-coupling reactions, such as Suzuki or Buchwald-Hartwig reactions, which are pivotal in medicinal chemistry.
Physical and Chemical Properties
The compound typically appears as an off-white to pale yellow crystalline powder with moderate stability under standard conditions. Its melting point decomposition around 200-205°C suggests thermal sensitivity, requiring careful handling during high-temperature reactions. Solubility is limited in polar protic solvents like water but improves in aprotic solvents such as DMSO or DMF. The bromine substituent enhances electrophilic reactivity compared to non-halogenated indolinones, while the lactam group contributes to hydrogen-bonding interactions—a feature exploited in molecular recognition processes.
Main Applications
In drug discovery, 5-bromoindolin-2-one acts as a precursor for kinase inhibitors and serotonin receptor modulators, where the indole core mimics tryptophan metabolites. Its bromine atom facilitates palladium-catalyzed couplings to introduce aryl or alkyl groups during lead optimization. Agrochemical applications include derivatization into herbicidal or fungicidal compounds. Additionally, it serves in material science for synthesizing organic semiconductors, where brominated intermediates enable controlled polymerization or side-chain modifications.
Safety and Storage
As a brominated organic compound, it requires precautions against inhalation, ingestion, and skin contact. SDS recommendations include using nitrile gloves, safety goggles, and respiratory protection when handling powders. Spills should be contained with inert absorbents. Long-term storage demands moisture-proof containers (e.g., vacuum-sealed bags) under refrigerated conditions (2-8°C) to prevent degradation. Amber glass vials are preferred to minimize photolytic decomposition. Incompatibilities include strong oxidizers and reactive metals.
B2B Procurement Guide
Bulk purchasers should verify supplier certifications (e.g., ISO 9001) and request batch-specific certificates of analysis (COA) detailing purity (HPLC/GC), residual solvents, and heavy metal content. Custom synthesis options may be available for derivatives or scaled quantities (>1 kg). Logistics considerations include cold-chain shipping for international orders and compliance with regional chemical regulations (e.g., REACH, TSCA). Sample quantities (1-10g) are typically offered for R&D validation before larger purchases. Lead times vary from 2-6 weeks depending on supplier inventory.
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